JP2017031060A - Cyclic depsipeptide derivative and pest control agent comprising the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel cyclic depsipeptide derivative and a pest control agent comprising the same.SOLUTION: The present invention provides a compound represented by a formula (1) or a stereoisomer thereof, and a pest control agent comprising the same.SELECTED DRAWING: None

Description

  The present invention relates to a cyclic depsipeptide derivative and a novel pest control agent using the same.

  Many pest control agents have been found so far, but new drugs are still required due to problems such as a decrease in drug sensitivity, long-lasting effects, and safety during use.

  Non-Patent Document 1 and Non-Patent Document 2 have reports on cyclic octadepsipeptides, but there is no disclosure of the compound of the present invention, and no suggestion is made about the pest control effect of the compound of the present invention.

  Non-Patent Document 3, Non-Patent Document 4, and Non-Patent Document 5 disclose the structures of cyclic octadepsipeptides and derivatives thereof, and their insecticidal activity against silkworms, but do not disclose the compounds of the present invention. It does not suggest the pest control effect of the compounds of the invention.

  Patent Documents 1, 2, and 3 disclose cyclic octadepsipeptides and their endoparasite control effects, but there is no disclosure of the compounds of the present invention, suggesting the pest control effects of the compounds of the present invention. is not.

  Patent Documents 4, 5, and 6 disclose cyclic octadepsipeptides as endoparasite control agents, but there is no disclosure of the compound of the present invention, and it does not suggest the pest control effect of the compound of the present invention. Absent.

  Patent Document 7 discloses FKI-1033 substance as a cyclic octadepsipeptide and discloses the inhibitory effect of ryanodine receptor. However, there is no disclosure of the compound of the present invention, and the pest control effect of the compound of the present invention is disclosed. It is not a suggestion.

  Patent Document 8 discloses a cyclic octadepsipeptide and its insecticidal activity against silkworms, scallops, and pinewood nematodes, but there is no disclosure of the compound of the present invention, which suggests the pest control effect of the compound of the present invention. is not.

European Patent Application Publication No. 0382173 Japanese Patent Laid-Open No. 05-229997 International Publication No. 93/19053 European Patent Application No. 0 626 376 European Patent Application No. 0626375 International Publication No. 2011/069995 International Publication No. 2004/44214 Japanese Patent Laid-Open No. 05-271013

Tetrahedron Letters (1963), 4 (6), 351 Tetrahedron Letters (1963), 4 (14), 885 Tetrahedron Letters (1977), 18 (25), 2167 Agricultural and Biological Chemistry (1978), 42 (3), 629 Peptide Chemistry (1978), 16th, 165

  An object of this invention is to provide a novel pesticidal agent.

  The present inventors have found a novel cyclic depsipeptide derivative, and have found that the cyclic depsipeptide derivative has an excellent activity as a pest control agent. The present invention is based on this finding.

That is, according to the present invention, the following inventions are provided.
(1) The following formula (1):

［式中、
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、ノルマルプロピル基、イソブチル基、ｓ−ブチル基、またはネオペンチル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、炭素数３〜７の直鎖アルキル基を示し（ただし、Ｒ₂およびＲ₄は、互いに同一であり、Ｒ₆およびＲ₈は、それぞれ、Ｒ₂およびＲ₄とは同一であっても異なっていてもよいが、Ｒ₆とＲ₈とは互いに異なる）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、それぞれ、水素原子またはメチル基を示す（ただし、Ｒ'₁およびＲ'₂は、互いに同一であり、Ｒ'₃およびＲ'₄は、それぞれ、Ｒ'₁およびＲ'₂とは同一であっても異なっていてもよい）；
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、ノルマルプロピル基、イソブチル基、ｓ−ブチル基、またはネオペンチル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、炭素数３〜７の直鎖アルキル基を示し（ただし、Ｒ₂およびＲ₄は、互いに同一であり、Ｒ₆およびＲ₈は、それぞれ、Ｒ₂およびＲ₄とは同一であっても異なっていてもよい）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、それぞれ、水素原子またはメチル基を示す（ただし、Ｒ'₁およびＲ'₂は、互いに同一であり、Ｒ'₃およびＲ'₄は、それぞれ、Ｒ'₁およびＲ'₂とは同一であっても異なっていてもよいが、Ｒ'₃とＲ'₄とは互いに異なる）；あるいは
Ｒ₁およびＲ₃がノルマルプロピル基を示し、Ｒ₅が水素原子を示し、Ｒ₇がｓ−ブチル基またはネオペンチル基を示し、Ｒ₂，Ｒ₄，Ｒ₆およびＲ₈はノルマルペンチル基を示し、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄がメチル基を示す化合物。］で示される化合物またはその立体異性体。
（２）下記式（１）：

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. R ₆ and R ₈ are different from each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are identical to one another, R _'3 and R' ₄ are each, may be the same or different from the R _'1 and R'₂;
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. And R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are the same as each other, and R ′ ₃ and R _'4 are each, R' ₁ and R 'may be the ₂ different be the same but, R' different from each other and ₃ and R _'4 ); Or R ₁ and R ₃ represents an n-propyl group, R ₅ represents a hydrogen atom, R ₇ represents a s- butyl group or a neopentyl _{group, R 2, R 4, R} 6 and R ₈ are n-pentyl And a compound in which R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ represent a methyl group. Or a stereoisomer thereof.
(2) The following formula (1):

［式中、
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₂、Ｒ₄は互いに異なり、Ｒ₆はＲ₂、Ｒ₄およびＲ₈とは同一であっても異なっていてもよく、Ｒ₈はＲ₂、Ｒ₄およびＲ₆とは同一であっても異なっていてもよい）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、それぞれ、水素原子、メチル基、またはエチル基を示す（ただし、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄は互いに同一であっても異なっていてもよい）；あるいは
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₂、Ｒ₄、Ｒ₆、およびＲ₈は互いに同一であっても異なっていてもよい）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、それぞれ、水素原子、メチル基、またはエチル基を示す（ただし、Ｒ'₁、Ｒ'₂は互いに異なり、Ｒ'₃はＲ'₁、Ｒ'₂およびＲ'₄とは同一であっても異なっていてもよく、Ｒ'₄はＲ'₁、Ｒ'₂およびＲ'₃とは同一であっても異なっていてもよい）。］で示される化合物またはその立体異性体。
（３）（１）または（２）に記載の化合物またはその立体異性体を、少なくとも１種以上含んでなる、農園芸用有害生物防除剤。
（４）（１）または（２）に記載の化合物またはその立体異性体の有効量を、農園芸用有害生物またはその生育場所に適用することを含んでなる、農園芸用有害生物の防除方法。
（５）農園芸用有害生物防除剤を製造するための、（１）または（２）に記載の化合物またはその立体異性体の使用。
（６）農園芸用有害生物防除剤として使用するための、（１）または（２）に記載の化合物またはその立体異性体。
（７）下記の式（１ａ）：

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. An optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are different from each other, R ₆ may be the same as or different from R ₂ , R ₄ and R ₈ ; R ₈ may be the same as or different from R ₂ , R ₄ and R ₆ ), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom, a methyl group, or an ethyl group (provided that R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other) Or R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms. Or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is , R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain having 1 to 9 carbon atoms, branched or A cyclic alkyl group or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms is shown (however, _2, R _4, R _6, and R ₈ may being the same or different), _{and, R '1, R' 2} , R '3, and R' ₄ are each a hydrogen atom, Represents a methyl group or an ethyl group (provided that R ′ ₁ and R ′ ₂ are different from each other; R ′ ₃ may be the same as or different from R ′ ₁ , R ′ ₂ and R ′ ₄ ; R ′ ₄ may be the same or different from R ′ ₁ , R ′ ₂ and R ′ ₃ ). Or a stereoisomer thereof.
(3) An agricultural and horticultural pest control agent comprising at least one of the compounds according to (1) or (2) or a stereoisomer thereof.
(4) A method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the compound according to (1) or (2) or a stereoisomer thereof to the agricultural or horticultural pests or their growing place. .
(5) Use of the compound according to (1) or (2) or a stereoisomer thereof for producing a pesticide for agricultural and horticultural use.
(6) The compound according to (1) or (2) or a stereoisomer thereof for use as an agricultural and horticultural pest control agent.
(7) The following formula (1a):

[式中、
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₂およびＲ₄は、互いに同一であり、Ｒ₆およびＲ₈は、それぞれ、Ｒ₂およびＲ₄とは同一であっても異なっていてもよい）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、それぞれ、水素原子、メチル基、またはエチル基を示す（ただし、Ｒ'₁およびＲ'₂は、互いに同一であり、Ｒ'₃およびＲ'₄は、それぞれ、Ｒ'₁およびＲ'₂とは同一であっても異なっていてもよい）；
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、互いに同一であり、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、互いに同一であり、水素原子、メチル基、またはエチル基を示す； あるいは
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁は、Ｒ₃、Ｒ₅およびＲ₇とは異なり、Ｒ₃、Ｒ₅およびＲ₇は、互いに同一である）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₄は、Ｒ₂、Ｒ₆およびＲ₈とは異なり、Ｒ₂、Ｒ₆およびＲ₈は、互いに同一であるか、あるいは、Ｒ₈は、Ｒ₂、Ｒ₄およびＲ₆とは異なり、Ｒ₂、Ｒ₄およびＲ₆は、互いに同一である）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、互いに同一であり、水素原子、メチル基、またはエチル基を示す。] で示される化合物;
下記式（１ｂ）：

[Where
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. Or an alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as R ₂ and R ₄ , respectively). it may be different), _{and, R '1, R' 2} , R '3, and R' ₄ are each, water Atom, a methyl group or an ethyl group, (wherein, R _'1 and R' ₂ are identical to one another, R _'3 and R' ₄ are each a same and R _'1 and R' ₂ Or different);
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, and are a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group having 1 to 9 carbon atoms, or Represents an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other, a hydrogen atom, a methyl group, or represents an ethyl group; or _{R 1, R 3, R 5} , and R ₇ are each a hydrogen atom, is substituted Linear which may having 1 to 9 carbon atoms have, branched, or indicates the cyclic alkyl group or an optionally substituted 2 to 9 carbon atoms alkoxyalkyl group, (wherein, R ₁ is, R _3, R ₅ and R ₇ , R ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom or an optionally substituted carbon number 1 to 9 linear, branched, or cyclic alkyl group, or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (provided that R ₄ is R ₂ , R _6, and R ₈ ; Unlike, R _2, R ₆ and R ₈ may be identical to each other, or, R ₈ is different from R _2, R ₄ and R _6, R _2, R ₄ and R ₆ are identical to each other ), _{and, R '1, R' 2} , R '3, and R' ₄ are identical to one another, a hydrogen atom, a methyl group Or an ethyl group. ] A compound represented by
The following formula (1b):

［式中、
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₂、Ｒ₄は互いに異なり、Ｒ₆はＲ₂、Ｒ₄およびＲ₈とは同一であっても異なっていてもよく、Ｒ₈はＲ₂、Ｒ₄およびＲ₆とは同一であっても異なっていてもよい）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、それぞれ、水素原子、メチル基、またはエチル基を示す（ただし、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄は互いに同一であっても異なっていてもよい）；あるいは
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁およびＲ₃は、互いに同一であり、Ｒ₅は、Ｒ₁およびＲ₃とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₂、Ｒ₄、Ｒ₆、およびＲ₈は互いに同一であっても異なっていてもよい）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、それぞれ、水素原子、メチル基、またはエチル基を示す（ただし、Ｒ'₁、Ｒ'₂は互いに異なり、Ｒ'₃はＲ'₁、Ｒ'₂およびＲ'₄とは同一であっても異なっていてもよく、Ｒ'₄はＲ'₁、Ｒ'₂およびＲ'₃とは同一であっても異なっていてもよい）。］で示される化合物；もしくは
下記式（１ｃ）：

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. An optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are different from each other, R ₆ may be the same as or different from R ₂ , R ₄ and R ₈ ; R ₈ may be the same as or different from R ₂ , R ₄ and R ₆ ), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom, a methyl group, or an ethyl group (provided that R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other) Or R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms. Or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is , R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain having 1 to 9 carbon atoms, branched or A cyclic alkyl group or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms is shown (however, _2, R _4, R _6, and R ₈ may being the same or different), _{and, R '1, R' 2} , R '3, and R' ₄ are each a hydrogen atom, Represents a methyl group or an ethyl group (provided that R ′ ₁ and R ′ ₂ are different from each other; R ′ ₃ may be the same as or different from R ′ ₁ , R ′ ₂ and R ′ ₄ ; R ′ ₄ may be the same or different from R ′ ₁ , R ′ ₂ and R ′ ₃ ). Or a compound represented by the following formula (1c):

［式中、
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁およびＲ₅は、互いに同一であり、Ｒ₃は、Ｒ₁およびＲ₅とは異なり、Ｒ₇は、Ｒ₁、Ｒ₃、Ｒ₅とは異なる）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、互いに同一であり、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、互いに同一であり、水素原子、メチル基、またはエチル基を示す；あるいは
Ｒ₁、Ｒ₃、Ｒ₅、およびＲ₇が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₁は、Ｒ₃、Ｒ₅およびＲ₇とは異なり、Ｒ₃、Ｒ₅およびＲ₇は、互いに同一である）、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈が、それぞれ、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し（ただし、Ｒ₆は、Ｒ₂、Ｒ₄およびＲ₈とは異なり、Ｒ₂、Ｒ₄およびＲ₈は、互いに同一である）、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄が、互いに同一であり、水素原子、メチル基、またはエチル基を示す。］で示される化合物
またはそれらの立体異性体を、少なくとも１種以上含んでなる、動物用寄生虫防除剤。
（８）（７）に記載の化合物またはその立体異性体の有効量を、動物用寄生虫またはその生育場所に適用することを含んでなる、動物用寄生虫の防除方法。
（９）（７）に記載の化合物またはその立体異性体の有効量を、寄生虫が寄生する動物に対して、体表面に適用することを含んでなる、動物用寄生虫の防除方法。
（１０）（７）に記載の化合物またはその立体異性体の有効量を、寄生虫が寄生する動物に対して、経口投与することを含んでなる、動物用寄生虫の防除方法。
（１１）動物用寄生虫防除剤を製造するための、（７）に記載の化合物またはその立体異性体の使用。
（１２）動物用寄生虫防除剤として使用するための、（７）に記載の化合物またはその立体異性体。

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₅ are the same as each other, R ₃ is different from R ₁ and R _5, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, and are a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group having 1 to 9 carbon atoms, or Represents an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other, a hydrogen atom, a methyl group, or represents an ethyl group; or _{R 1, R 3, R 5} , and R ₇ are each a hydrogen atom, is substituted Linear which may having 1 to 9 carbon atoms have, branched, or indicates the cyclic alkyl group or an optionally substituted 2 to 9 carbon atoms alkoxyalkyl group, (wherein, R ₁ is, R _3, R ₅ and R ₇ , R ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom or an optionally substituted carbon number 1 to 9 linear, branched, or cyclic alkyl group, or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (provided that R ₆ is R ₂ , R _4, and R ₈ ; R ₂ , R ₄ and R ₈ are the same as each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are the same as each other, and are a hydrogen atom, a methyl group, or An ethyl group is shown. ] The parasite control agent for animals which comprises at least 1 or more types of the compound shown by these, or those stereoisomers.
(8) A method for controlling animal parasites, which comprises applying an effective amount of the compound according to (7) or a stereoisomer thereof to the animal parasite or its place of growth.
(9) A method for controlling animal parasites, which comprises applying an effective amount of the compound according to (7) or a stereoisomer thereof to the body surface of an animal parasitized by parasites.
(10) A method for controlling animal parasites, comprising orally administering an effective amount of the compound according to (7) or a stereoisomer thereof to an animal parasitized by a parasite.
(11) Use of the compound according to (7) or a stereoisomer thereof for producing an animal parasite control agent.
(12) The compound according to (7) or a stereoisomer thereof for use as an animal parasite control agent.

  By using the compound according to the present invention, it is possible to effectively control many pests as agricultural and horticultural pest control agents and animal parasite control agents. In addition, it is advantageous in that it can be effectively controlled against drug-resistant pests.

Compounds of the Invention According to the invention, the following formula (1):

［式中、
Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅、Ｒ₆、Ｒ₇、およびＲ₈は、同一または異なっていてもよく、水素原子、置換されていてもよい炭素数１〜９の直鎖、分岐、もしくは環状のアルキル基、または置換されていてもよい炭素数２〜９のアルコキシアルキル基を示し、
Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄は、同一または異なっていてもよく、水素原子、メチル基、またはエチル基を示し（ただし、Ｒ₂、Ｒ₄、Ｒ₆、およびＲ₈がいずれもイソプロピル基を示す場合に、Ｒ₁、Ｒ₃、Ｒ₅、Ｒ₇がイソプロピル基またはイソブチル基を示す化合物；Ｒ₂、Ｒ₄、Ｒ₆、Ｒ₈がいずれもノルマルペンチル基を示す場合にＲ₁、Ｒ₃、Ｒ₅、Ｒ₇がいずれもメチル基を示す化合物；並びに、Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅、Ｒ₆、Ｒ₇、およびＲ₈がいずれもメチル基を示す化合物を除く）。］
で示される化合物またはその立体異性体が提供される。

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and are each a hydrogen atom or an optionally substituted straight chain having 1 to 9 carbon atoms. A chain, branched, or cyclic alkyl group, or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms;
R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ may be the same or different and each represents a hydrogen atom, a methyl group, or an ethyl group (provided that R ₂ , R ₄ , R ₆ , and when R ₈ is all exhibited an isopropyl _{group, R 1, R 3, R} 5, compound R ₇ represents an isopropyl group or isobutyl group; R _2, R _4, also R _6, R ₈ are all normal pentyl group Wherein R ₁ , R ₃ , R ₅ , R ₇ are all methyl groups; and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ Except for compounds in which each represents a methyl group). ]
Or a stereoisomer thereof is provided.

In the compound of the formula (1), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ represent “a linear, branched, or cyclic alkyl having 1 to 9 carbon atoms. The “group” means a linear group having 1 to 9 carbon atoms, or an alkyl group which may contain a branched or cyclic structure. The alkyl group is a saturated or unsaturated alkyl group, that is, an alkyl group that may contain one or more unsaturated bonds. When it contains a branched or cyclic structure or has an unsaturated bond, it is clear that the number of carbon atoms is 3 or more. Specific examples include methyl group, ethyl group, normal propyl group, isopropyl group, cyclopropyl group, normal butyl group, isobutyl group, sec-butyl group, cyclobutyl group, normal pentyl group, neopentyl group, cyclopentyl group, normal Examples thereof include a hexyl group, a 2-methylpentyl group, a normal heptyl group, a 2-methylhexyl group, a normal octyl group, and a normal nonyl group.

  Here, “optionally substituted” means one to three carbon atoms of a linear, branched or cyclic alkyl group having 1 to 9 carbon atoms, preferably one substituent. In this case, the “substituent” is, for example, a halogen atom, a hydroxyl group, a cyano group, a nitro group, or the like.

  In the present specification, the “halogen atom” means an atom selected from fluoro, chloro, bromo and iodo.

In the compound of the formula (1), “an alkoxyalkyl group having 2 to 9 carbon atoms” represented by R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ is an alkoxy group. Means an alkyl group having 2 to 9 carbon atoms in total in the alkoxy moiety and the alkyl moiety. Examples of the “alkoxy group” include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentyloxy, neopentyloxy, i-pentyloxy, t -Pentyloxy, n-hexyloxy, i-hexyloxy and the like. Specific examples include methoxymethyl group and ethoxymethyl group.

  Here, the term “which may be substituted” means that the number of carbon atoms in the alkoxyalkyl group having 2 to 9 carbon atoms (preferably the carbon atom of the alkoxy moiety) is 1 to 3, preferably 1. The “substituent” is, for example, a halogen atom, a cyano group, a nitro group, or the like.

In the compound of the formula (1), R ₁ , R ₃ , R ₅ , and R ₇ are preferably a hydrogen atom or an optionally substituted linear, branched or cyclic alkyl having 1 to 7 carbon atoms. Group, more preferably a hydrogen atom or an optionally substituted linear or branched alkyl group having 1 to 5 carbon atoms, and further preferably a hydrogen atom or optionally substituted 3 to 3 carbon atoms. 5 linear or branched alkyl groups, specifically, hydrogen atom, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, sec-butyl group, isobutyl group, neopentyl group, etc. It is done.

In the compound of the formula (1), R ₂ , R ₄ , R ₆ and R ₈ are preferably a linear alkyl group having 1 to 9 carbon atoms or a branched or cyclic alkyl group having 4 to 8 carbon atoms. More preferably, it is a linear alkyl group having 3 to 9 carbon atoms or a branched or cyclic alkyl group having 4 to 8 carbon atoms, and more preferably a linear alkyl group having 3 to 9 carbon atoms. And even more preferably, a straight-chain alkyl group having 3 to 7 carbon atoms, specifically, a normal propyl group, a normal butyl group, a normal pentyl group, a normal hexyl group, a normal heptyl group, and the like.

In the compound of the formula (1), R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are a hydrogen atom, a methyl group or an ethyl group, preferably a hydrogen atom or a methyl group.

As the compound according to the present invention, preferably, R ₁ , R ₃ , R ₅ , and R ₇ may be the same or different, a hydrogen atom, or an optionally substituted straight chain having 1 to 7 carbon atoms, A branched or cyclic alkyl group; R ₂ , R ₄ , R ₆ , and R ₈ may be the same or different, and are a linear alkyl group having 1 to 9 carbon atoms or a branched chain having 4 to 8 carbon atoms; Or a cyclic alkyl group; R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ _{4, which} may be the same or different, are a hydrogen atom, a methyl group, or an ethyl group; And the compounds represented.

As the compound according to the present invention, more preferably, R ₁ , R ₃ , R ₅ , and R ₇ may be the same or different, a hydrogen atom, or an optionally substituted straight chain having 1 to 5 carbon atoms. Or a branched alkyl group; R ₂ , R ₄ , R ₆ , and R ₈ may be the same or different and are a linear alkyl group having 3 to 9 carbon atoms; R ′ ₁ , R ′ ₂ R ′ ₃ and R ′ ₄ may be the same or different and include a compound represented by the formula (1), which is a hydrogen atom or a methyl group.

More preferably, as the compound according to the present invention, R ₁ , R ₃ , R ₅ , and R ₇ may be the same or different, a hydrogen atom, or an optionally substituted straight chain having 3 to 5 carbon atoms. Or a branched alkyl group; R ₂ , R ₄ , R ₆ , and R ₈ may be the same or different and are a linear alkyl group having 3 to 7 carbon atoms; R ′ ₁ , R ′ ₂ R ′ ₃ and R ′ ₄ may be the same or different and include a compound represented by the formula (1), which is a hydrogen atom or a methyl group.

  As a first aspect of the compound of the above formula (1), a compound in which the octadepsipeptide chain constituting the ring is of the -A-A-B-C-type or -B-A-A-C-type (No. Compound of one embodiment). In the present specification, the compound of the first aspect may be represented as a compound represented by the formula (1a).

In particular,
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. Or an alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as R ₂ and R ₄ , respectively). it may be different), _{and, R '1, R' 2} , R '3, and R' ₄ are each, water Atom, a methyl group or an ethyl group, (wherein, R _'1 and R' ₂ are identical to one another, R _'3 and R' ₄ are each a same and R _'1 and R' ₂ Or different);
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, and are a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group having 1 to 9 carbon atoms, or Represents an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other, a hydrogen atom, a methyl group, or represents an ethyl group; or _{R 1, R 3, R 5} , and R ₇ are each a hydrogen atom, is substituted Linear which may having 1 to 9 carbon atoms have, branched, or indicates the cyclic alkyl group or an optionally substituted 2 to 9 carbon atoms alkoxyalkyl group, (wherein, R ₁ is, R _3, R ₅ and R ₇ , R ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom or an optionally substituted carbon number 1 to 9 linear, branched, or cyclic alkyl group, or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (provided that R ₄ is R ₂ , R _6, and R ₈ ; Unlike, R _2, R ₆ and R ₈ may be identical to each other, or, R ₈ is different from R _2, R ₄ and R _6, R _2, R ₄ and R ₆ are identical to each other ), _{and, R '1, R' 2} , R '3, and R' ₄ are identical to one another, a hydrogen atom, a methyl group Or an ethyl group, a compound of formula (1).

Preferably,
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom or an optionally substituted linear or branched alkyl group having 3 to 5 carbon atoms (provided that R ₁ and R ₃ are R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are respectively Represents a linear alkyl group having 3 to 7 carbon atoms (provided that R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ are the same as or different from R ₂ and R ₄ , respectively) R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are the same as each other). And R ′ ₃ and R ′ ₄ may be the same or different from R ′ ₁ and R ′ ₂ , respectively);
R ₁ , R ₃ , R ₅ and R ₇ each represent a hydrogen atom or a linear, branched or cyclic alkyl group having 3 to 7 carbon atoms (provided that R ₁ and R ₃ are the same as each other). R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, carbon A linear alkyl group of 5 to 7 and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are identical to each other and represent a methyl group; or R ₁ , R ₃ , R ₅ and R ₇ each represent a hydrogen atom or a linear, branched or cyclic alkyl group having 3 to 7 carbon atoms (provided that R ₁ is different from R ₃ , R ₅ and R ₇ ; _3, R ₅ and R ₇ are identical to each _{other), R 2, R 4,} R 6 and R ₈ are each an alkyl group of a straight chain having 5 to 7 carbon atoms However, R ₄ is different from R _2, R ₆ and R _8, R _2, R ₆ and R ₈ may be identical to each other, or, R ₈ is a R _2, R ₄ and R ₆ R ₂ , R ₄ and R ₆ are the same as each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are the same as each other and represent a methyl group, It is a compound of 1).

More preferably,
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. And R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are the same as each other, and R ′ ₃ And R ′ ₄ may be the same or different from R ′ ₁ and R ′ ₂ , respectively);
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, carbon A linear alkyl group of 5 to 7 and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are identical to each other and represent a methyl group; or R ₁ , R ₃ , R ₅ and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ is different from R ₃ , R _5, and R ₇ ; ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each a carbon number A linear alkyl group having 5 to 7 (wherein, R ₄ is different from R _2, R ₆ and R _8, or R _2, R ₆ and R ₈ are identical to each other, or, R ₈ Unlike R _2, R ₄ and R _6, R _2, R ₄ and R ₆ are identical to each other), _{and, R '1, R' 2} , R '3, and R' ₄ is, Compounds of formula (1) which are identical to each other and represent a methyl group.

More preferably,
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. And R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are the same as each other, and R ′ ₃ And R ′ ₄ may be the same or different from R ′ ₁ and R ′ ₂ , respectively; or R ₁ and R ₃ are Represents a normal propyl group, R ₅ represents a hydrogen atom, R ₇ represents a s-butyl group or a neopentyl group, R ₂ , R ₄ , R ₆ and R ₈ represent a normal pentyl group, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are methyl compounds.

Even more preferably,
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. R ₆ and R ₈ are different from each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are identical to one another, R _'3 and R' ₄ are each, may be the same or different from the R _'1 and R'₂;
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. And R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are the same as each other, and R ′ ₃ and R _'4 are each, R' ₁ and R 'may be the ₂ different be the same but, R' different from each other and ₃ and R _'4 ); Or R ₁ and R ₃ represents an n-propyl group, R ₅ represents a hydrogen atom, R ₇ represents a s- butyl group or a neopentyl _{group, R 2, R 4, R} 6 and R ₈ are n-pentyl And a compound of formula (1) wherein R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ represent a methyl group.

As the compound of the first aspect, preferably, R ₁ and R ₃ represent a normal propyl group, and R ₅ and R ₇ are different from each other, and represent a hydrogen atom, an isobutyl group, an s-butyl group, or a neopentyl group. R ₂ and R ₄ represent a normal pentyl group, R ₆ and R ₈ are the same or different and represent a normal propyl group, a normal pentyl group, or a normal heptyl group, and R ′ ₁ and R ′ ₂ Represents a methyl group, R ′ ₃ and R ′ ₄ are different from each other to represent a hydrogen atom or a methyl group; or R ₁ and R ₃ represent a normal propyl group, and R ₅ and R ₇ are different from each other. A hydrogen atom, an isobutyl group, an s-butyl group, or a neopentyl group, R ₂ and R ₄ represent a normal pentyl group, R ₆ and R ₈ are different from each other, a normal propyl group, a normal pentyl group, Or Indicates Rumaruhepuchiru group, and, R _'1, R' ₂ represents a methyl group, R _'3, R' ₄ are the same or different, represent a hydrogen atom or a methyl group, is a compound of formula (1) .

As the compound of the first aspect, more preferably, R ₁ and R ₃ represent a normal propyl group, R ₅ represents a hydrogen atom, R ₇ represents an isobutyl group, a s-butyl group, or a neopentyl group, R ₂ and R ₄ represent a normal pentyl group, R ₆ and R ₈ are the same or different and represent a normal propyl group, a normal pentyl group or a normal heptyl group, and R ′ ₁ and R ′ ₂ are methyl. R ′ ₃ and R ′ ₄ are different from each other and represent a hydrogen atom or a methyl group; alternatively, R ₁ and R ₃ represent a normal propyl group, R ₅ represents a hydrogen atom, and R ₇ represents An isobutyl group, a s-butyl group or a neopentyl group; R ₂ and R ₄ represent a normal pentyl group; R ₆ and R ₈ are different from each other, and represent a normal propyl group, a normal pentyl group or a normal heptyl group; Indication And R ′ ₁ and R ′ ₂ represent a methyl group, and R ′ ₃ and R ′ ₄ are the same or different and represent a hydrogen atom or a methyl group, and are compounds of formula (1).

As the compound of the first embodiment, preferably, R ₁ and R ₃ represent normal propyl, R ₅ represents a hydrogen atom, R ₇ represents an isobutyl group, R ₂ , R ₄ , R ₆ and The compound of the formula (1), wherein R ₈ represents a normal pentyl group, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ represent a methyl group.

  As a 2nd aspect of the compound of Formula (1), the compound (compound of a 2nd aspect) whose octadepsipeptide chain | strand which comprises a ring is -ABCDD type is mentioned. In the present specification, the compound of the second aspect may be represented as a compound represented by the formula (1b).

In particular,
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. An optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are different from each other, R ₆ may be the same as or different from R ₂ , R ₄ and R ₈ ; R ₈ may be the same as or different from R ₂ , R ₄ and R ₆ ), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom, a methyl group, or an ethyl group (provided that R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other) Or R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms. Or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is , R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain having 1 to 9 carbon atoms, branched or A cyclic alkyl group or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms is shown (however, _2, R _4, R _6, and R ₈ may being the same or different), _{and, R '1, R' 2} , R '3, and R' ₄ are each a hydrogen atom, Represents a methyl group or an ethyl group (provided that R ′ ₁ and R ′ ₂ are different from each other; R ′ ₃ may be the same as or different from R ′ ₁ , R ′ ₂ and R ′ ₄ ; R ′ ₄ may be the same or different from R ′ ₁ , R ′ ₂ and R ′ ₃ ), and is a compound of the formula (1).

Preferably,
R ₁ , R ₃ , R ₅ and R ₇ each represent a hydrogen atom or a linear, branched or cyclic alkyl group having 3 to 7 carbon atoms (provided that R ₁ and R ₃ are the same as each other). R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are different from each other, R ₆ may be the same as or different from R ₂ , R ₄ and R _8, and R ₈ is R ₂ , R ₄ and R ₆ may be the same or different, and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ each represent a hydrogen atom or a methyl group ( R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ may be the same or different from each other); or R ₁ , R ₃ , R ₅ , and R ₇ are respectively Each represents a hydrogen atom or a linear, branched or cyclic alkyl group having 3 to 7 carbon atoms (provided that R ₁ and R ₃ are the same as each other; R ₅ is different from R ₁ and R ₃ ; R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ each represent a linear alkyl group having 3 to 7 carbon atoms (provided that R ₂ , R ₄ , R ₆ , and R ₈ may be the same or different from each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are each a hydrogen atom or methyl R ′ ₁ and R ′ ₂ are different from each other, R ′ ₃ may be the same as or different from R ′ ₁ , R ′ ₂ and R ′ _4, and R ′ ₄ is R ' ₁ , R' ₂ and R ' ₃ may be the same or different) and are compounds of formula (1).

More preferably,
R ₁ , R ₃ , R ₅ and R ₇ each represent a hydrogen atom or a linear or branched alkyl group having 3 to 5 carbon atoms (provided that R ₁ and R ₃ are the same as each other; R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R _6, and R ₈ are each having 3 to 7 carbon atoms. (Wherein R ₂ and R ₄ are different from each other, R ₆ may be the same as or different from R ₂ , R ₄ and R ₈ , R ₈ is R ₂ , R ₄ and R ₆ may be the same or different, and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that , R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ may be the same or different from each other); or R ₁ , R ₃ , R ₅ , and R ₇ are each Represents a hydrogen atom or a linear or branched alkyl group having 3 to 5 carbon atoms (wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is , R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R _6, and R ₈ each represent a linear alkyl group having 3 to 7 carbon atoms (provided that R ₂ , R ₄ , R ₆ , and R ₈ may be the same or different from each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group. (However, R ′ ₁ and R ′ ₂ are different from each other, R ′ ₃ may be the same as or different from R ′ ₁ , R ′ ₂ and R ′ _4, and R ′ ₄ is R ′ ₁ , R ′ ₂ and R ′ ₃ may be the same or different, and are compounds of formula (1).

More preferably,
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, or an isobutyl group (provided that R ₁ and R ₃ are the same as each other, and R ₅ represents R ₁ and Unlike R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are each a linear alkyl group having 3 to 7 carbon atoms. shows (Unlike R _2, R ₄ are each, R ₆ may be the be the same or different and R _2, R ₄ and R _8, R ₈ and R _2, R ₄ and R ₆ R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ , R ′ may be the same or different). ₂ , R ′ ₃ , and R ′ ₄ may be the same or different from each other); or R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, A normal propyl group or an isobutyl group (wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ and R ₂ , R ₄ , R ₆ and R ₈ are each a straight chain alkyl group having 3 to 7 carbon atoms (provided that R ₂ , R ₄ , R ₆ and R ₈ are the same as each other). And R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ , R ′ ₂ identical to are different from each other, R _'3 is R' _1, R _'2 and R' ₄ may be different even in the same and, R _'4 is R' _1, R _'2 and R' ₃ Or may be different), a compound of formula (1).

As the compound of the second embodiment, preferably, R ₁ and R ₃ represent a normal propyl group, R ₅ and R ₇ are different from each other and represent a hydrogen atom or an isobutyl group, and R ₂ , R ₄ , R ₆ , R ₈ represents a normal propyl group, a normal pentyl group, or a normal heptyl group (provided that R ₂ and R ₄ are different from each other, and R ₆ is the same as R ₂ , R ₄ and R _8). R ₈ may be the same as or different from R ₂ , R ₄ and R ₆ ), and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are A hydrogen atom or a methyl group (wherein R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ may be the same or different from each other); or R ₁ and R ₃ are normal propyl represents a group, R _5, R ₇ are different from each other, a hydrogen atom or an isobutyl group, R _2, R _{4, 6,} R ₈ are n-propyl group, n-pentyl group or indicates normal heptyl group _{(, R 2, R 4, R} 6, and R ₈ may being the same or different), and , R ′ ₁ , R ′ ₂ , R ′ ₃ , R ′ ₄ represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are different from each other, and R ′ ₃ represents R ′ ₁ , R ′ _2). and R _'4 may be different even in the same and, R' may be different even identical and ₄ R _'1, R' ₂ and R _'3), the formula (1) It is a compound of this.

As the compound of the second embodiment, more preferably, R ₁ and R ₃ represent a normal propyl group, R ₅ and R ₇ are different from each other and represent a hydrogen atom or an isobutyl group, and R ₂ , R ₄ , R ₆ and R ₈ represent a normal propyl group, a normal pentyl group, or a normal heptyl group (provided that R ₂ and R ₄ are different from each other, and R ₆ is the same as R ₂ , R ₄ and R _8). R ₈ may be the same as or different from R ₂ , R ₄ and R ₆ ), and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are R ₁ and R ₃ each represent a normal propyl group; R ₅ and R ₇ are different from each other and represent a hydrogen atom or an isobutyl group; and R ₂ , R ₄ , R ₆ , R ₈ but shows a normal pentyl _{group, R '1, R' 2} , R '3, R' 4 is a hydrogen atom or a methyl group Be (provided that, R _'1, R' ₂ are different from each other, R _'3 is R' or different and be identical to the _1, R _'2 and R' _4, R _'4 is R' ₁ , R ′ ₂ and R ′ ₃ may be the same or different, and are compounds of formula (1).

  As a third embodiment of the compound of the formula (1), a compound in which the octadepsipeptide chain constituting the ring is -ABACA type or -BACA type (third type). Compound of the embodiment). In the present specification, the compound of the third aspect may be represented as a compound represented by the formula (1c).

In particular,
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₅ are the same as each other, R ₃ is different from R ₁ and R _5, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, and are a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group having 1 to 9 carbon atoms, or Represents an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other, a hydrogen atom, a methyl group, or represents an ethyl group; or _{R 1, R 3, R 5} , and R ₇ are each a hydrogen atom, is substituted Linear which may having 1 to 9 carbon atoms have, branched, or indicates the cyclic alkyl group or an optionally substituted 2 to 9 carbon atoms alkoxyalkyl group, (wherein, R ₁ is, R _3, R ₅ and R ₇ , R ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom or an optionally substituted carbon number 1 to 9 linear, branched, or cyclic alkyl group, or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (provided that R ₆ is R ₂ , R _4, and R ₈ ; R ₂ , R ₄ and R ₈ are the same as each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are the same as each other, and are a hydrogen atom, a methyl group, or It is a compound of formula (1) showing an ethyl group.

Preferably,
R ₁ , R ₃ , R ₅ and R ₇ each represent a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 7 carbon atoms (provided that R ₁ and R ₅ are the same as each other). , R ₃ is different from R ₁ and R ₅ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are identical to each other, carbon A linear alkyl group of 5 to 7 and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are identical to each other and represent a methyl group; or R ₁ , R ₃ , R ₅ and R ₇ each represent a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 7 carbon atoms (provided that R ₁ is different from R ₃ , R ₅ and R ₇ ; ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ each represents a linear alkyl group having 5 to 7 carbon atoms ( However, R ₆ is different from R _2, R ₄ and R _8, R _2, R ₄ and R ₈ are identical to each other), _{and, R '1, R' 2} , R '3, and R ' ₄ is a compound of the formula (1), which are identical to each other and represent a methyl group.

More preferably,
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a methyl group, a normal propyl group, an isobutyl group, or a neopentyl group (provided that R ₁ and R ₅ are the same as each other, R ₃ is different from R ₁ and R ₅ , R ₇ is different from R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R _6, and R ₈ are the same as each other and have 5 carbon atoms A linear alkyl group of ˜7, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are identical to each other and represent a methyl group; or R ₁ , R ₃ , R ₅ , And R ₇ each represent a hydrogen atom, a methyl group, a normal propyl group, an isobutyl group, or a neopentyl group (provided that R ₁ is different from R ₃ , R _5, and R _7, and R ₃ , R ₅ And R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each of 5 to 7 carbon atoms An alkyl group of straight-chain (where, R ₆ is different from R _2, R ₄ and R _8, R _2, R ₄ and R ₈ are identical to each other), and, R _'1, R' ₂ , R ′ ₃ and R ′ ₄ are compounds of formula (1) wherein they are identical to each other and represent a methyl group.

As the compound of the third aspect, preferably, R ₁ and R ₅ represent a normal propyl group, R ₃ represents a hydrogen atom, R ₇ represents an isobutyl group, R ₂ , R ₄ , R ₆ and R The compound of the formula (1) in which ₈ represents a normal pentyl group and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ represent a methyl group.

  Specific examples of the compound represented by the formula (1) are shown in Table 1.

なお、表中のＲ₂、Ｒ₄、Ｒ₆およびＲ₈のＣ３〜７はそれぞれ直鎖のアルキル基を示す。

Incidentally, showing the R _2, R _4, R ₆ and C3~7 alkyl group of each linear R ₈ in the table.

Examples of the compound of the first aspect (compound represented by formula (1a)) include, for example, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R _{8 in} formula (1). , R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ can be used in combination with the compounds shown in Compound Nos. 1, 2, 4, 5, 7 and 12-14 in Table 1. it can. Examples of the compound of the first aspect (compound represented by the formula (1a)) include, for example, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ in the formula (1), A compound in which the combination of R ₈ , R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ _{4 is} a combination shown in Compound No. 15 in Table 1 can be used.

Examples of the compound of the second embodiment (the compound represented by the formula (1b)) include R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R _{8 in} the formula (1). , R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ can be used in the combinations shown in Compound Nos. 3, 6, 8 to 11 and 17 in Table 1.

Examples of the compound of the third aspect (compound represented by formula (1c)) include, for example, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R _{8 in} formula (1). , R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ can be used in the combination shown in Compound No. 16 in Table 1.

Although various isomers exist in the compound of the formula (1), the present invention includes both the isomers and a mixture thereof. In addition, the presence of isomers attributed to other groups in formula (1) is also conceivable, but these isomers and mixtures thereof are also encompassed in formula (1).
Production of the Compound of the Present Invention The compound according to the present invention can be produced according to “Basics and Experiments of Peptide Synthesis” (Nobuo Izumiya, Tetsuo Kato, Toshihiko Aoyagi, Noriaki Wakido, Maruzen, 1985).

  Hereinafter, the production method will be specifically described in detail.

  The compound of formula (1) above is represented by formula (2):

[式中、Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅、Ｒ₆、Ｒ₇、Ｒ₈、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄は、上記で定義された内容と同義である。]で示される化合物（直鎖オクタデプシペプチド）を環化することにより製造することができる。具体的には、式（２）の化合物を、適当な縮合剤を用いて、塩基性反応助剤の存在下、希薄溶液となるように適当な不活性溶媒を加えて、反応させることにより得ることができる。

[Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are defined above] It is synonymous with the contents. ] (A linear octadepsipeptide) can be produced by cyclization. Specifically, the compound of formula (2) is obtained by reacting with a suitable condensing agent by adding a suitable inert solvent so as to form a dilute solution in the presence of a basic reaction aid. be able to.

  Examples of the condensing agent include all condensing agents suitable for producing an amide bond. For example, carbodiimide condensing agents such as dicyclohexylcarbodiimide (DCC) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 1,1′-carbonyldiimidazole (CDI), 2-chloro- Imidazolium-based condensing agents such as 1,3-dimethylimidazolinium hexafluorophosphate (CIP), 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP), bromotris hexafluorophosphate ( Examples thereof include phosphonium salt condensing agents such as pyrrolidino) phosphonium (PyBrop), and EDCI and PyBOP are preferred.

  Examples of basic reaction aids include basic compounds such as amidine base and guanidine base, such as 7-methyl-1,5,7-triazabicyclo (4.4.0) dec-5-ene (MTBD): Diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) -octane (BCO), 1,8-diaza-bicyclo (5.4.0) undecene (DBU), cyclohexyl-tetrabutyl Guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N, N, N, N-tetramethyl-1,8-naphthalenediamine, pentamethylpiperidine, tertiary amines, triethylamine, trimethylamine, tribenzylamine, tribenzylamine Isopropylamine, tributylamine, tribenzylamine, tricyclohexylamine, Liamylamine, trihexylamine, N, N-dimethyl-aniline, N, N-dimethyl-toluidine, N, N-dimethyl-p-aminopyridine, N-methyl-pyrrolidine, N-methyl-piperidine, N-methyl-imidazole N-methyl-pyrrole, N-methyl-morpholine, N-methyl-hexamethyleneimine, pyridine, 4-pyrrolidinopyridine, 4-dimethylamino-pyridine, quinoline, α-picoline, β-picoline, isoquinoline, pyrimidine, Acridine, N, N, N ′, N′-tetramethylenediamine, N, N ′, N′-tetraethylenediamine, quinoxaline, N-propyl-diisopropylamine, N-ethyl-diisopropylamine, N, N′-dimethylcyclohexyl Amine, 2,6-lutidine, 2,4-lutidi Or triethylenediamine, and the like, preferably, trialkylamines such as triethylamine, N, N-diisopropylethylamine, N-propyl-diisopropylamine, N, N′-dimethyl-cyclohexylamine or N-methylmorpholine. .

  Any solvent may be used as long as it does not inhibit the dehydration condensation reaction. For example, tetrachloroethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichloroethylene, pentachloroethane, difluorobenzene, 1, Halogenated hydrocarbons such as 2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene, ethylpropyl ether, methyl tert-butyl ether, n-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether , Dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diiso Ethers such as mill ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane, amines such as trimethyl-, triethyl-, tripropyl-, tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine, methyl acetate, ethyl acetate, acetic acid Esters such as butyl, isobutyl acetate, dimethyl carbonate, dibutyl carbonate, ethylene carbonate, hexamethylene phosphate triamide, formamide, N-methyl-formamide, N 2, N-dimethylformamide, N, N-dipropylformamide, N, N -Dibutylformamide, N-methylpyrrolidine, N-methyl-caprolactam, 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidine, octylpyrrolidone, octylcaprola Amides such as cutam, 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, N, N′-1,4-diformylpiperazine, and ketones such as acetone, acetophenone, methyl ethyl ketone, and methyl butyl ketone Preferred are halogen-based hydrocarbons such as dichloromethane. These reaction solvents can be used alone or in combination.

  The amount of the condensing agent used is in the range of 1 to 20 times by weight of the compound of the formula (2), preferably in the range of 1 to 5 times by weight.

  The usage-amount of a basic reaction adjuvant is the range of 0.01-50 weight times of the compound of Formula (2), Preferably, it is the range of 0.01-10 weight times.

  The amount of reaction solvent used is in the range of 50 to 1000 times by weight of the compound of formula (2), preferably in the range of 100 to 500 times by weight.

  The reaction temperature is in the range of −10 ° C. to 100 ° C., preferably in the range of −10 ° C. to 40 ° C.

  The compound of formula (2) is represented by formula (3):

[式中、Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅、Ｒ₆、Ｒ₇、Ｒ₈、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄は、上記で定義された内容と同義であり、Ｘは、アセチル（Ａｃ）、アリルオキシカルボニル（Ａｌｌｏｃ）、ベンジルオキシカルボニル（ＣｂＺ）、ｔｅｒｔ−ブチルオキシカルボニル（Ｂｏｃ）、９−フルオレニルメチルオキシカルボニル（Ｆｍｏｃ）などの選択的に除去可能なＮ末端保護基を表し、Ｙは、ベンジル（Ｂｎ）、ｐ−ニトロベンジル（Ｎｂ）、ｔｅｒｔ−ブチル（ｔ−Ｂｕ）、３，４，５−トリス（オクタデシロキシ）ベンジル（Ｔａｇ）などの選択的に除去可能なＣ末端保護基、選択的に除去可能な固定基を伴う重合体の支持体を表わす。]の化合物から、Ｘ基およびＹ基を適当な条件下で除去することにより得ることができる。

[Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are defined above] X is acetyl (Ac), allyloxycarbonyl (Alloc), benzyloxycarbonyl (CbZ), tert-butyloxycarbonyl (Boc), 9-fluorenylmethyloxycarbonyl (Fmoc), etc. Wherein Y represents benzyl (Bn), p-nitrobenzyl (Nb), tert-butyl (t-Bu), 3,4,5-tris (octadecyloxy) ) Represents a polymeric support with a selectively removable C-terminal protecting group, such as benzyl (Tag), and a selectively removable fixing group. ] Can be obtained by removing the X group and the Y group from the compound under the appropriate conditions.

  Depending on the type of the X and Y groups, the X and Y groups can be removed by acid decomposition in the presence of a protonic acid, β-elimination under mild basic conditions, and appropriate under a hydrogen gas atmosphere. It can be carried out by catalytic reduction using a catalyst.

  For acid decomposition, for example, a reactant obtained by introducing hydrogen chloride gas such as HCl / ethyl acetate or HCl / dioxane into an organic solvent is used as it is, or trifluoroacetic acid is used as it is or a solvent that does not inhibit the reaction, for example, methylene chloride. In addition, halogen-based hydrocarbons such as chloroform and carbon tetrachloride, and aromatic hydrocarbon-based solvents such as benzene and toluene can be used.

  β-elimination (for example, removal of Fmoc) is carried out by using piperazine using aprotic polar solvents such as N, N-dimethylformamide and halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride. Secondary amines such as diethylamine can be used.

  The amount of the solvent used is in the range of 1 to 200 times by weight of the compound of the formula (3), preferably in the range of 2 to 50 times by weight.

  The reaction temperature is in the range of 0 ° C to 50 ° C, preferably in the range of 0 ° C to room temperature.

  The catalytic reduction is carried out in a solvent using a catalyst in the presence or absence of an acid or an alkali in a hydrogen gas atmosphere.

  The solvent used for the catalytic reduction may be any solvent as long as it does not inhibit the reaction. For example, alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, methyl acetate, ethyl acetate, butyl acetate, etc. Examples include esters. These reaction solvents can be used alone or mixed with water.

  The amount of the solvent used is in the range of 1 to 200 times by weight, preferably in the range of 2 to 50 times by weight of the compound of formula (3).

  Examples of the catalyst used for catalytic reduction include metal-containing compounds such as 5% palladium carbon, 10% palladium carbon, and Raney nickel.

  The amount of the catalyst used is in the range of 1% to 100% by weight of the compound of the formula (3), preferably in the range of 1% to 20% by weight.

  Examples of the acid or alkali used for catalytic reduction include hydrochloric acid, hydrobromic acid, hydroiodic acid, mineral acids such as nitric acid, sulfuric acid and phosphoric acid, organic acids such as acetic acid and methanesulfonic acid, sodium hydroxide, Examples include inorganic bases such as potassium hydroxide, calcium hydroxide, and aqueous ammonia.

  The reaction temperature is in the range of room temperature to 200 ° C., and the hydrogen pressure is in the range of normal pressure to 150 atm.

The compound of formula (3) can be synthesized by several methods. Hereinafter, three methods (steps (A) to (C)) will be exemplified.
Step (A)
The compound of the formula (3) can be produced by reacting hexadepsipeptide and didepsipeptide. Specifically, the compound of formula (3) is represented by formula (4):

[式中、Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅、Ｒ₆、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＸは、上記で定義された内容と同義である。]で示される化合物（ヘキサデプシペプチド）と、
式（５）：

[Wherein, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ′ ₁ , R ′ ₂ , R ′ ₃ , and X are as defined above]. ] A compound (hexadepsipeptide) represented by
Formula (5):

[式中、Ｒ₇、Ｒ₈、Ｒ'₄、およびＹは、上記で定義された内容と同義である。]で示される化合物（ジデプシペプチド）とを反応させることにより製造することができる。

[Wherein R ₇ , R ₈ , R ′ ₄ , and Y have the same meaning as defined above. ] Can be produced by reacting with a compound (didepsipeptide).

  Specifically, by reacting the compound of the above formula (4) and the compound of the above formula (5) by adding a suitable solvent in the presence of a basic reaction aid using a suitable condensing agent. Can be manufactured.

  As the appropriate condensing agent and basic reaction aid, those described above can be used.

  As the solvent, a solvent that can be used in the cyclization reaction can be used.

  The amount of the condensing agent used is in the range of 1 to 20 times by weight, preferably in the range of 1 to 5 times by weight that of the compound of formula (4).

  The usage-amount of a basic reaction adjuvant is the range of 0.01-50 weight times of the compound of Formula (4), Preferably, it is the range of 0.01-10 weight times.

  The amount of the reaction solvent used is in the range of 1 to 200 times by weight, preferably in the range of 2 to 50 times by weight of the compound of the formula (4).

The reaction temperature is in the range of −10 ° C. to 100 ° C., preferably in the range of −10 ° C. to 40 ° C.
Process (B)
The compound of formula (3) can be produced by reacting two tetradepsipeptides which may be the same or different. Specifically, the compound of formula (3) is represented by formula (6)

[式中Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ'₁、Ｒ'₂、およびＸは、上記で定義された内容と同義である。]で示される化合物（テトラデプシペプチド）と、
式（７）：

[Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ′ ₁ , R ′ ₂ , and X have the same meaning as defined above] ] A compound (tetradepsipeptide) represented by
Formula (7):

[式中Ｒ₅、Ｒ₆、Ｒ₇、Ｒ₈、Ｒ'₃、Ｒ'₄、およびＹは、上記で定義された内容と同義である。]で示される化合物（テトラデプシペプチド）とを反応させることにより製造することができる。

[Wherein R ₅ , R ₆ , R ₇ , R ₈ , R ′ ₃ , R ′ ₄ , and Y have the same meaning as defined above] It can manufacture by making the compound (tetradepsipeptide) shown by these react.

The reaction conditions are the same as those in step (A).
Process (C)
The compound of formula (3) can also be produced by a solid phase synthesis method using a polymer support with a selectively removable fixing group, as shown in Scheme 1 below.

（スキーム中、Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅、Ｒ₆、Ｒ₇、Ｒ₈、Ｒ'₁、Ｒ'₂、Ｒ'₃、Ｒ'₄およびＸは、上記で定義された内容と同義であり、ＰＳは、ポリスチレン樹脂を表わす。）
選択的に除去可能な固定基を伴う重合体の支持体とは、有機溶媒や試薬に対する耐性を持った樹脂（例えば、ジビニルベンゼン等で架橋したポリスチレン、ポリエチレングリコール−ポリスチレン等）に、樹脂と化合物をつなぐための固定基（例えば、２−クロロトリチル、ヒドロキシメチルフェノール等）を担持させたものであり、例えば、２−クロロトリチルクロロレジン等が挙げられる。

(In the scheme, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ′ ₁ , R ′ ₂ , R ′ ₃ , R ′ ₄ and X are defined above. (PS stands for polystyrene resin.)
A polymer support with a selectively removable fixing group is a resin having resistance to organic solvents and reagents (eg, polystyrene cross-linked with divinylbenzene, polyethylene glycol-polystyrene, etc.), resin and compound And a fixing group (for example, 2-chlorotrityl, hydroxymethylphenol, etc.) for connecting the two, such as 2-chlorotrityl chlororesin.

  The compound of formula (4) (hexadepsipeptide) is composed of the compound of formula (6) (tetradepsipeptide) and formula (9):

（式中、Ｒ₅、Ｒ₆、Ｒ'₃、およびＹは、上記で定義された内容と同義である。）で示される化合物（ジデプシペプチド）とを、上記工程（Ａ）と同様の反応条件で反応させることによって得ることができる式（１０）：

(Wherein R ₅ , R ₆ , R ′ ₃ , and Y have the same meanings as defined above) and a compound (didepsipeptide) represented by the same reaction as in the above step (A) Formula (10) that can be obtained by reacting under conditions:

（式中、Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ₅、Ｒ₆、Ｒ'₁、Ｒ'₂、Ｒ'₃、Ｘ、およびＹは、上記で定義された内容と同義である。）
の化合物から、式（３）の化合物から式（２）の化合物を合成する前記の方法と同様の反応条件によって、Ｙ基を除去することによっても得ることができる。

(Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ′ ₁ , R ′ ₂ , R ′ ₃ , X, and Y have the same meaning as defined above. .)
It can also be obtained by removing the Y group under the same reaction conditions as in the above-described method for synthesizing the compound of formula (2) from the compound of formula (3).

  The compound represented by formula (6) (tetradepsipeptide) is represented by the formula (11):

（式中、Ｒ₁、Ｒ₂、Ｒ'₁、およびＸは、上記で定義された内容と同義である。）で示される化合物（ジデプシペプチド）と式（１２）：

(Wherein R ₁ , R ₂ , R ′ ₁ , and X are as defined above) and a compound (didepsipeptide) represented by the formula (12):

（式中、Ｒ₃、Ｒ₄、Ｒ'₂、およびＹは、上記で定義された内容と同義である。）で示される化合物（ジデプシペプチド）とを、上記工程（Ａ）と同様の反応条件で反応させることによって得ることができる式（１３）：

(Wherein R ₃ , R ₄ , R ′ ₂ , and Y have the same meanings as defined above) and a compound (didepsipeptide) represented by the same reaction as in the above step (A) Formula (13) that can be obtained by reacting under conditions:

（式中、Ｒ₁、Ｒ₂、Ｒ₃、Ｒ₄、Ｒ'₁、Ｒ'₂、Ｘ、およびＹは、上記で定義された内容と同義である。）の化合物から、式（３）の化合物から式（２）の化合物を合成する前記の方法と同様の反応条件によって、Ｙ基を除去することによっても得ることができる。

(Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ′ ₁ , R ′ ₂ , X and Y have the same meaning as defined above), the compound of formula (3) It can also be obtained by removing the Y group under the same reaction conditions as in the method for synthesizing the compound of formula (2) from the compound of

  Similarly, the compound of formula (7) (tetradepsipeptide) also has the corresponding formula (14)

（式中、Ｒ₅、Ｒ₆、Ｒ'₃、およびＸは、上記で定義された内容と同義である。）で示される化合物（ジデプシペプチド）と式（５）で示される化合物（ジデプシペプチド）とを反応させて得られる化合物（テトラデプシペプチド）である式（１５）：

(Wherein R ₅ , R ₆ , R ′ ₃ , and X have the same meaning as defined above) and a compound represented by formula (5) (didepsipeptide) ) Is a compound (tetradepsipeptide) obtained by reacting with (15):

（式中、Ｒ₅、Ｒ₆、Ｒ₇、Ｒ₈、Ｒ'₃、Ｒ'₄、Ｘ、およびＹは、上記で定義された内容と同義である。）の化合物から、式（３）の化合物から式（２）の化合物を合成する前記の方法と同様の反応条件によって、Ｘ基を除去することによっても得ることができる。

(Wherein R ₅ , R ₆ , R ₇ , R ₈ , R ′ ₃ , R ′ ₄ , X, and Y have the same meaning as defined above), from the compound of formula (3) It can also be obtained by removing the X group under the same reaction conditions as in the above method for synthesizing the compound of formula (2) from the compound of

The dedepsipeptides of formula (9), formula (11), formula (12), and formula (14) each have an amino group-protected α-amino acid in which the corresponding amino group is substituted with R ′ ₁ to R ′ ₄ , α It can be synthesized by condensing a hydroxycarboxylic acid ester with an appropriate condensing agent. Alternatively, it can be synthesized by deprotecting the N-terminal protecting group or the C-terminal protecting group of the didepsipeptide protected at the N-terminus and C-terminus.

  Commercially available N-substituted N-protected α-amino acids used as raw materials for didepsipeptides can be used as they are, and commercially available α-amino acids protected with protecting groups such as Boc or CbZ can be used as alkylating agents such as alkyl halides. Those alkylated with can be used. Alternatively, the amino group of a free amino acid may be protected with a protecting group such as Boc or CbZ and then alkylated with an alkylating agent such as an alkyl halide.

  The α-hydroxycarboxylic acid used as a raw material for didepsipeptide is represented by the following scheme 2:

（スキーム中、Ｒ₂、およびＹは、上記で定義された内容と同義である。）に示されるような市販のα−アミノ酸を用いた既知の方法（Brewster, P., et al. Nature 1950, 166, 179-180. Lerchen, H. G. et al. Tetrahedron Lett. 1985, 26, 5257-5260）で合成できる。

(In the scheme, R ₂ and Y have the same meanings as defined above.) Known methods using commercially available α-amino acids as shown in (Brewster, P., et al. Nature 1950 166, 179-180. Lerchen, HG et al. Tetrahedron Lett. 1985, 26, 5257-5260).

  Or the following scheme 3:

（スキーム中、Ｒ₂、およびＹは、上記で定義された内容と同義である。）に示したDavis試薬を用いた方法（Souichi Monma et al. Org. Lett., Vol. 8, No. 24, 2006）で合成できる。

(In the scheme, R ₂ and Y have the same meaning as defined above) (Souichi Monma et al. Org. Lett., Vol. 8, No. 24) , 2006).

  Alternatively, the following scheme 4:

（スキーム中、Ｒ₂、およびＹは、上記で定義された内容と同義である。）に示すＬ−セリンを出発原料にした合成法で得ることが出来る。
有害生物防除剤
式（１）の化合物は、有害生物防除剤として用いることができる。

(In the scheme, R ₂ and Y have the same meanings as defined above), and can be obtained by a synthesis method using L-serine as a starting material.
The compound of the pest control agent formula (1) can be used as a pest control agent.

  In the present specification, the term “pest control agent” means a drug exhibiting a pest control effect, and includes not only a drug that kills pests but also a drug that suppresses the growth of pests. Here, the “pest” refers to a living organism that causes adverse effects on human health, economic activity, and the like. Pests include agricultural and horticultural pests, animal parasitic pests, satellite pests, unpleasant pests, stored grain pests, stored food pests, house pests, and the like.

  Pest control agents provided by the present invention include, for example, agricultural and horticultural pest control agents (eg, agricultural and horticultural insecticides, agricultural and horticultural acaricides), animal parasite control agents (eg, animal Internal parasite control agent, animal ectoparasite control agent, etc.), sanitary pest control agent, unpleasant pest control agent, stored grain / stored food pest control agent, house pest control agent, etc. Among them, preferred are agricultural and horticultural insecticides, agricultural and horticultural acaricides, animal parasite control agents, sanitary pest control agents, and unpleasant pest control agents.

  Examples of insect species in which a pest control agent comprising at least one compound represented by the formula (1) exhibits a controlling effect are as follows.

  Agricultural and horticultural pests include lepidopterous pests (for example, Lotus spider, Coleoptera, Acacia, Aomushi, Konaga, Shirochimogiyoto, Nikameiga, Kofomomeiga, Futabikogaga, Clamidae, Sinkiga, Clamidae, Agrotis sp.) Pests (Helicoverpa spp), Heliothis spp, etc., Hemiptera pests (eg, peach aphids, cotton aphids, black aphids, corn aphids, pea aphids, potato aphids, bean aphids, tulip beetles) , Commaphidia, Methopolophium dirhodum, Euglena aphid, Euglena aphid, Japanese aphid aphid, Snowy aphid, Rosy apple Aphid, apple aphid, rice aphid, citrus aphid, etc. (Aphididae, Adelgidae, Phy11oxeridae), leafhoppers such as leafhopper leafhoppers, chanomidorihimebikoba, leafhoppers such as leafhoppers, leafhoppers, leafworms Stink bugs such as stink bugs, Chabanae stink bugs, red beetle buttercups, silver leaf whiteflies, tobacco whiteflies, whitefly whiteflies (A1eyrodidae), stag beetles, citrus scales Diaspididae, Margarodidae, Ortheziidae, Ac1erdiae, Dacty1opiidae, Kerridae, Pseudococcidae, Coccidae, Eriococcidae, Asterolecaniidae, Beesonidae, Lecanodiaspididae, Cerococcidae Crustacea pests (eg, rice weevil, azuki bean weevil, brown rice weevil, western corn root worm, southern corn root worm, sand squirrel, sand squirrel) , Plant parasitic mite pests (eg, urticae, kanzawa spider mites, citrus mite, tomato rust mites, citrus mites), hymenoptera (eg, wasps), straight moth (eg, grasshopper), dipterous pests (eg, grasshopper) For example, house flies and leafhoppers), thrips pests (for example, southern thrips, citrus thrips, etc.), plant parasitic nematodes (for example, root-knot nematodes, nesting nematodes, rice-singing nematodes) And pine wood nematode).

  Preferred examples include lepidopterous insects, semilepidopterous insects, Coleoptera insects, plant parasitic mite insects, diptera insects, and thrips insects. More preferably, lepidopterous insects, semilepidopterous insects, thrips insect pests, and plant parasitic mite insect pests.

  Specific examples of insect pests include diamondback moth, cotton aphid, on-whitefly, citrus white thrips, red-bellied thrips, nymph mite, kanzawa spider mite, citrus spider mite, and the like.

  Animal parasitic pests include animal parasitic mite pests (eg, ticks) (eg, Lone star ticks, Gulf of Mexico ticks, ticks, Rocky Mountain ticks, west coast ticks, American dog ticks, ticks, ticks) Tick, Tick, Tick, Tick, Tick, Western Black Mite, Schulze mite, Sheep Tick, Black Mite, Tiger Tick, Cray mite Tick, Preacarid (e.g., Mites, Mites, Mites, Mites) For example, acarid mites, pistol mites, lepidopterids, tsutsugamushi (for example, Miyamatsu tsutsugamushi, red tsutsugamushi)), anatomicals (for example, cucumber mites (for example, bovine cucumber) Mite), hymenidae (for example, oxenid mite, mite mite), canary mite (for example, avian mite), mites (for example, fowl mite, mite mite), angiidae, flea (for example, cat flea) Human fleas, keops mud mines, mud mines), lice (e.g., white lice (e.g., dog lice, chicken lice), louses (e.g., pork louse, dog lice, lop lice), fly flies (e.g., flies) House flies, cattle flies, sand flies, fountains, butterflies (eg, sand flies), tsetse flies, aphids, aedes (eg, Aedes albopictus, Aedes aegypti), squids (eg, Acacia), anopheles, nukaca Euphoridae), stink bugs (for example, sand turtles), nematodes (for example fecal nematodes, helminths, roundworms (for example tortuous stomachs, murine worms), ciliate nematodes, strange Roundworms (eg, porcine pneumoniae, Cantonese schistosomiasis, cat lungworm), helminths, caecals (eg, chicken roundworm), roundworms (eg, Anisakis nematode, pig roundworm, horse roundworm, dog) Roundworm, cat roundworm, etc. (for example, burula, spiny jaw-mouth beetle, cat stomachworm, horoscope stomachworm, large mouth horse stomachworm, chicken stomachworm, medinaworm), filamentous worms ( For example, canine filamentous worms, lymphoid filamentous worms, rotiferous worms, loar filamentous worms), nematodes, trichinidae (for example, dog whiskers, trichinella)), flukes (for example, Schistosoma japonicum, liver fluke) ), Bald worms, tapeworms (for example, suspicious leaves (for example, Manson fissures), circles (for example, Candida)), protozoa, and the like.

  Hygiene pests, unpleasant pests, stored grain pests, stored food pests, and house pests include cockroaches (eg, black cockroaches, cockroaches, German cockroaches), coniferous mites (eg, staghorn), fly flies (eg, housefly) , Drosophila, butterflies, Drosophila, Chironomidae), Cyprinidae, Papilioceae, Cucurbitaceae (eg, Aedes albopictus, Culex), Hymenoptera insects (eg, Ants such as Crested ant, fire ant, etc., Bees such as giant hornet) ), Artemipods of the order of Paramecium (eg, Paramecium, Funabushi, Dangamushi), insects of the order Hemiptera (eg, bed bugs), Arthropods of polypods (eg, centipedes, geese, millipedes), spiders Arthropods of the eye (for example, Ashida spider), Coleoptera insects (for example, wormworm), Arthropods of the order of Coleoptera ( For example, staghorn beetles), earworms (for example, giant beetles), grasshoppers (for example, caterpillars), coleopterous insects (for example, azuki beetle, weevil, scorpion, scorpion, leopard beetle, beetle , Cutworms, black-winged beetles), lepidopterous insects (for example, moths, moths), broad-billed insects, termite insects (for example, termites, American white termites, taiwan termites), blemis (for example, Yamatoshimi), etc. It is done.

  Preferable examples include animal parasitic mites, fleas, nematodes, ciliate nematodes, eclipsoids, helminths, caecals, and flies.

  Specific pests include ticks, fleas, house flies, nematodes and the like.

  In addition to the compound represented by the formula (1), the pest control agent of the present invention can be prepared using a pharmaceutically acceptable additive according to the method of use.

  When the pest control agent according to the present invention is used as an agricultural and horticultural pest control agent, as a pharmaceutical additive, a solid carrier, a liquid carrier, a gaseous carrier, a surfactant, a dispersing agent, and other formulation adjuvants And can be provided as dosage forms such as emulsions, liquids, suspensions, wettable powders, flowables, powders, granules, tablets, oils, aerosols and smokes.

  Examples of the solid carrier include talc, bennite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.

  Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methylnaphthalene. Aromatic hydrocarbons such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean oil , Vegetable oils such as cottonseed oil, dimethyl sulfoxide, water and the like.

  Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.

  Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, A lignin sulfonate can be used.

  As an auxiliary agent for preparation for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like can be used.

  The above carriers, surfactants, dispersants, and formulation adjuvants can be used alone or in combination as necessary.

  The content of the active ingredient in the preparation is not particularly limited, but is usually 1 to 75% by weight for emulsions, 0.3 to 25% by weight for powders, 1 to 90% by weight for wettable powders, and 0 for granules. 5 to 10% by weight.

  The pest control agent according to the present invention or a mixture with other pest control agents described later includes harmful insects, plants, plant propagation materials (eg, seeds, plant foliage, roots, germinated plants, And young plants), soil, nutrient solution in hydroponic culture, solid medium in hydroponic culture, and rooms that need to prevent the invasion of pests.

  These applications can be made before and after pest infestation.

  In particular, the pesticidal agent according to the present invention, or a mixture with other pesticidal agents described later, is an effective amount of plant seeds, roots, tubers, bulbs, rhizomes, germinated plants, seedlings, soil, Pests can be controlled by applying to a target selected from the group consisting of a nutrient solution in hydroponic culture and a solid medium in hydroponic culture, and osmotically transferred into the plant.

  When the application target is plant seeds, roots, tubers, bulbs or rhizomes, suitable examples of application methods are not particularly limited as long as they do not impede osmotic transfer, but immersion methods, powder coating methods, smearing methods , Spraying method, pellet method, coating method and the like.

  In the case of seeds, application methods include, for example, a dipping method, a powder coating method, a smearing method, a spraying method, a pellet method, a film method, and a fumigation method. The dipping method is a method in which seeds are immersed in a liquid drug solution. The powder coating method includes a dry powder coating method in which a powdered drug is attached to dry seeds, and a seed lightly soaked in water. There is a wet powder coating method to attach the drug in the shape. In addition, there are a smearing method in which a suspended drug is applied to the seed surface in a mixer and a spraying method in which the suspension is sprayed onto the seed surface. In addition, when pelletizing seeds with a filler into a certain size and shape, the pellet method in which the filler is mixed with the chemical, the coating method in which the seed is coated with a film containing the chemical, and in a sealed container A fumigation method that disinfects seeds with gasified chemicals can be mentioned.

  When applied to germinated plants and seedlings, these plants can be protected by application after sprouting, emergence from the soil, and before transplanting by whole or partial treatment by soaking .

  In addition, when applied to seeds, roots, tubers, bulbs, rhizomes, etc., plant or immerse the seeds, roots, tubers, bulbs, rhizomes, etc. for a time sufficient for the drug to penetrate into the plant. Also mentioned. In this case, the immersion time and temperature are appropriately determined by those skilled in the art according to the application target, the type and amount of the drug, and the like. And although it does not specifically limit as penetration transfer time, For example, it is 1 hour or more. Moreover, as temperature in osmosis | permeation transfer, it is 5-45 degreeC, for example.

  As an application method to soil, for example, a pesticide according to the present invention or a granule of a mixture with other pest control agents described later may be applied in or on the soil. Preferred soil application methods are spraying, strips, grooves, and planting hole application methods. Here, the spraying treatment includes surface treatment over the entire area to be treated and subsequent mechanical introduction into the soil.

  It is also an advantageous soil application method to apply by irrigating the soil with a solution obtained by emulsifying or dissolving a pest control agent according to the present invention or a mixture with other pest control agents described later in water.

  When applied to nutrient solutions in hydroponic culture systems such as hydroponics and sand culture, NFT (Nutrient Film Technique), rock medium cultivation, etc. for the production of vegetables and flowers It is also clear that the pest control agent according to the present invention or a mixture with other pest control agents described later can be directly applied to an artificial soil containing vermiculite and a solid medium containing an artificial mat for raising seedlings.

  In the application step, the effective amount of the compound of formula (1) or a stereoisomer thereof is preferably an amount sufficient for the compound of formula (1) to permeate into the plant in the subsequent permeation transition step. .

  The effective amount can be appropriately determined in consideration of the nature of the compound, the type and amount of the object to be applied, the length of the subsequent osmotic transfer step, temperature, etc. For example, in the case of seeds, the formula (1) The amount of the compound or stereoisomer thereof is preferably 1 g to 10 kg, more preferably 10 g to 1 kg, per 10 kg of seeds.

  Moreover, when applying to soil, the quantity of the compound of Formula (1) or its stereoisomer is preferably 0.1 to 10 kg, more preferably 1 to 1 kg per 10 ares of arable land. When processing to the foliage part of a plant, the amount of the compound of the formula (1) or a stereoisomer thereof is preferably 0.1 g to 10 kg, more preferably 1 g to 1 kg per 10 ares of cultivated land. desirable.

  When the pest control agent of the present invention is used as an animal parasitic pest control agent, it is a solution, emulsion, liquefied drop, spray, foam preparation, tablet, granule, fine granule, powder, capsule, round Agents, chewables, injections, suppositories, creams, shampoos, rinses, resin agents, smokers, poison baits, etc., but liquids, liquefied drops, tablets, granules, More preferably, it is provided in fine granules, capsules, pills, chewables.

  The liquid preparation can further contain formulation additives such as emulsifiers, dispersants, spreading agents, wetting agents, suspending agents, preservatives, propellants and the like as pharmaceutical additives. A film-forming agent can also be blended. Surfactants for emulsification, dispersion, spreading, etc. include, for example, soaps, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene alkyl allyl ethers, polyoxyethylene fatty acid esters, higher alcohols, alkylaryls A sulfonate or the like can be used. Examples of the dispersant include casein, gelatin, polysaccharides, lignin derivatives, saccharides, and synthetic water-soluble polymers. Examples of spreading / wetting agents include glycerin and polyethylene glycol. Examples of the suspending agent include casein, gelatin, hydroxypropyl cellulose, and gum arabic. Examples of the stabilizing agent include phenolic antioxidants (BHT, BHA, etc.) and amine antioxidants (diphenylamine, etc.). ) And organic sulfur-based antioxidants. Examples of the preservative include methyl paraoxybenzoate, ethyl paraoxybenzoate, propyl paraoxybenzoate, and butyl paraoxybenzoate. The above carriers, surfactants, dispersants, and adjuvants can be used alone or in combination as required. Furthermore, you may contain a fragrance | flavor, a synergist, etc. The content of the active ingredient in the pesticidal composition of the present invention is usually 1 to 75% by weight in a liquid preparation.

  Examples of the carrier used for preparing the cream include non-volatile hydrocarbons (such as liquid paraffin), lanolin-added oils and fats, higher fatty acids, fatty acid esters, animal and vegetable oils, silicone oils, and water. Furthermore, emulsifiers, moisturizers, antioxidants, fragrances, borax, and ultraviolet absorbers can be used alone or in combination as required. Examples of the emulsifier include fatty acid sorbitan, polyoxyethylene alkyl ether, and fatty acid polyoxyethylene. The content of the active ingredient in the pest control agent of the present invention is usually 0.5 to 70% by weight for creams.

  For capsules, pills or tablets, the active ingredient in the composition of the present invention is appropriately subdivided and mixed with a diluent or a carrier such as starch, lactose, talc, and a disintegrant such as magnesium stearate. And / or a binder can be added and used as a tablet if necessary.

  Injections must be prepared as sterile solutions. An injection may contain, for example, sufficient salt or glucose to make the solution isotonic with blood. Carriers that can be used to prepare injectables include glycerides, esters such as benzyl benzoate, isopropyl myristate and fatty acid derivatives of propylene glycol, organic solvents such as N-methylpyrrolidone, glycerol formal. The content of the active ingredient in the pest control agent of the present invention is usually 0.01 to 10% by weight for injections.

  Examples of the carrier for preparing the resin agent include vinyl chloride polymers and polyurethane. If necessary, plasticizers such as phthalates, adipic esters, and stearic acid can be added to these substrates. After kneading the active ingredient in the substrate, it can be molded by injection molding, extrusion molding, press molding or the like. Furthermore, it can be made into an animal ear tag or an animal insect repellent collar through appropriate steps such as molding, cutting and cutting.

  Carriers for poisonous baits include dietary substances and attractants (flours such as wheat flour and corn flour, starches such as corn starch and potato starch, sugars such as granulated sugar, maltose and honey, foods such as glycerin, onion flavor and milk flavor. And animal powders such as flavors, rice cake powders, and fish meals, and various pheromones). The content of the active ingredient of the pest control agent of the present invention is usually 0.0001 to 90% by weight for poison baits.

  The pest control agent according to the present invention or a mixture with other pest control agents described later may be administered orally or by injection into the body of the applied animal, or administered to the whole or part of the body surface of the applied animal. Can control pests. In addition, by coating the pest control agent according to the present invention or a mixture with other pest control agents described later with the pest control agent of the present invention where the invasion, parasitism, and migration are expected. It can also control pests.

  The pest control agent of the present invention may be used as it is, but depending on the case, it can be diluted with water, a liquid carrier, a commercially available shampoo, rinse, bait, a breeding house underlay or the like.

  The pest control agent according to the present invention includes other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, animal parasite control agents, sanitary pest control agents, unpleasant pest control agents, It can also be used by mixing with stored and stored food pest control agents, house pest control agents and the like.

  Drugs that can be used in combination include those listed in the Pesticide Manual (published by The British Crop Protection Council 13th edition) and Shibuya Index (published by SHIBUYA INDEX 16th edition, 2012, published by SHIBUYA INDEX RESEARCH GROUP). It is done.

More specifically, examples of the drug that can be used by mixing include the following drugs (A-1) to (A-26).
(A-1) Organic phosphate ester compounds include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenofos, pyraclofos , Chlorpyrifos-methyl, diazinon, fosthiazate, imicyafos, trichlorfon, tetrachlorvinphos, bromofenofos, cythioate It is done.
(A-2) Carbamate compounds include mesomyl, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, and ethiofencarb. , Fenothiocarb, pirimicarb, carbofuran, benfuracarb, and triazamate.
(A-3) Pyrethroid insecticides include acrinathrin, allethrin, bifenthrin, bioallethrin, bioresmethrin, cyfluthrin, cyphenothrin ( cyphenothrin), empetrin (empenthrin), flumethrin (flumethrin), halfenprox (halfenprox), imiprothrin, methfluthrin (metofluthrin), phenothrin (phenothrin), praretrin (prallethrin), profluthrin (refluthrin, refluthrin) Resmethrin, tetramethrin, tralomethrin, transfluthrin, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin, cyhalothrin (fenvale rate), fluvalinate, etofenprox, silafluofen, phthalthrin, pyrethrum extract, sinepirin 222, synepirin 500.
(A-4) Juvenile hormone-like compounds include hydroprene, metoprene, kinoprene, fenoxycarb, and pyriproxyfen.
(A-5) Nicotine receptor agonists and antagonists include cartap, thiocyclam, bensultap, thiosultap, imidacloprid, clothianidin, thiamethoxam, acetamiprid, acetamiprid (Acetamiprid), nitenpyram, thiacloprid, dinotefuran, spinosad, spinetram, sulfoxaflor, flupyradifurone, levamisole hydrochloride, levamosole hydrochloride Examples include acid pyrantel, pyrantel, and monepantel.
(A-6) GABAergic chloride channel antagonists include ethiprole, fipronil, pyrafluprole, pyriprole, and endosulfan.
(A-7) Chloride channel acting compounds include abamectin, milbemectin, lepimectin, emamectin benzoate, ivermectin, selamectin, moxidectin, moxidectin , Doramectin, eprinomectin, milbemycin oxime.
(A-8) Examples of the mitochondrial respiratory chain complex I inhibitor include pyridaben, fenpyroxymate, pyrimidifen, tebufenpyrad, tolfenpyrad, and fenazaquin.
(A-9) Examples of mitochondrial respiratory chain complex II inhibitors include cyenopyrafen, piflbumide, and cyflumetofen.
(A-10) Mitochondrial respiratory chain complex III inhibitors include fluacrypyrim, acequinocyl, and hydramethylnon.
(A-11) An example of the uncoupler is chlorfenapyr.
(A-12) Other oxidative phosphorylation inhibitors include azocyclotin, cyhexatin, diafenthiuron, fenbutatin oxide, propargite, tetradifon Is mentioned.
(A-13) Examples of molting inhibitors include cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide.
(A-14) As a synergist, piperonyl butoxide (piperonyl butoxide) and tribufos (tribufos) are mentioned.
(A-15) Examples of sodium channel inhibitors include indoxacarb and metaflumizone.
(A-16) Examples of the fumigant include methyl bromide and chloropicrin sulfuryl fluoride.
(A-17) Selective feeding inhibitors include crylotie, pymetrozine, flonicamid.
(A-18) Examples of mite growth inhibitors include clofentezine, hexythiazox, and ethoxazole.
(A-19) Chitin biosynthesis inhibitors include buprofezin, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron ( Examples include flufenoxuron, hexaflumuron, lufenuron, novaluron, noiflumuron, teflubenzuron, triflumuron.
(A-20) Examples of lipid biosynthesis inhibitors include spirodiclofen, spiromesifen, and spirotetramat.
(A-21) Examples of octopamine-like substances include amitraz, chlordimeform, and demiditraz.
(A-22) The ryanodine receptor agonist may be flubendiamide.
(A-23) As the isoxazole derivative, 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2-methyl-N-pyridin- 2-ylmethyl-benzamide), 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2-methyl-N- (2,2, 2-trifluoro-ethyl) -benzamide, 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2-methyl-N-[(2 , 2,2-trifluoro-ethylcarbamoyl) -methyl] -benzamide, 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -naphthalene-1 -carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl) -methyl] -amide, 4- [5- (3,5-Dichlorophenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -N-[(methoxyimino) methyl] -2-methylbenzamide, 4- [5- (3-Chloro-5-trifluoromethyl-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2- methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl) -methyl] -benzamide, 4- [5- (3-Chloro-5-trifluoromethyl-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol -3-yl] -naphthalene-1-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl) -me thyl] -amide or 5- [5- (3,5-Dichloro-4-fluoro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2- [1,2, 4] triazol-1-yl-benzonitrile.
(A-24) As anthranilic acid amide compounds, chlorantraniliprole, cyantraniliprole, cyclaniliprole, substances represented by the following formulas or acid addition salts thereof Is mentioned.

（Ａ−２５）微生物殺虫剤としては、Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Tenebrionisが挙げられる。
（Ａ−２６）その他の殺虫剤としては、ジコホル(dicofol)、ビフェナゼート（bifenazate）、ピリダリル（pyridalyl）、または、ピリフルキナゾン（pyrifluquinazon）、フロメトキン（flometoquin）、アフィドピロペン(afidopyropen)、トリフルメゾピリム(triflumezopyrim)、アミドフルメト(amidoflumet)、ディート（deet）、メトキサジアゾン（metoxadiazon）、スターアニス油（star anise oil）、トリクラベンダゾール（triclabendazole）、フルベンダゾール（flubendazole）、フェンベンダゾール（fenbendazole）、グルコン酸アンチモンナトリウム（antimony sodium gluconate）、ビチオノール（bithionol）、ジクロロフェン（dichlorofen）、フェノチアジン（phenothiazine）、二硫化炭素ピペラジン（piperazine carbon bisulfide）、リン酸ピペラジン（piperazine phosphate）、アジピン酸ピペラジン（piperazine adipate）、クエン酸ピペラジン（piperazine citrate）、メラルソミン二塩酸塩（melarsomine dihydrochloride）、メチリジン（metyridine）、サントニン（santonin）、プラジクアンテル（praziquantel）、フェバンテル（febantel）、エモデプシド（emodepside）、メラルソニル(melarsonyl)、ジエチルカルバミジン(dietylcarbamazine)、有機金属系化合物、ジニトロ系化合物、有機硫黄化合物、尿素系化合物、トリアジン系化合物、ヒドラジン系化合物、下記の式で示される物質またはそれらの酸付加塩：

(A-25) Examples of the microbial insecticide include Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Tenebrionis.
(A-26) Other insecticides include dicofol, bifenazate, pyridalyl, pyrifluquinazon, flometoquin, afidopyropen, triflumezopyrim (triflumezopyrim) , Amidoflumet, deet, metoxadiazon, star anise oil, triclabendazole, flubendazole, fenbendazole, antimony sodium gluconate ( antimony sodium gluconate, bithionol, dichlorofen, phenothiazine, piperazine carbon bisulfide, piperazine phosphate, piperazine adi pate, piperazine citrate, melarsomine dihydrochloride, metyridine, santonin, praziquantel, febantel, emodepside, melarsonyl, melarsonyl Diethylylcarbamazine, organometallic compounds, dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds, substances represented by the following formulas or their acid addition salts:

[式中、
Ａｒは、ハロゲン原子、水酸基、もしくはハロゲン原子により置換されていてもよいＣ₁〜₆アルキル基、ハロゲン原子により置換されていてもよいＣ₁〜₆アルキルオキシ基、シアノ基、またはニトロ基で置換されていてもよいピリジル基；あるいは、ハロゲン原子、ハロゲン原子により置換されていてもよいＣ₁〜₄アルキル基、ハロゲン原子により置換されていてもよいＣ₁〜₄アルキルオキシ基、水酸基、シアノ基、またはニトロ基で置換されていてもよいピリミジル基を示し、
Ｙは、水素原子、ハロゲン原子、水酸基、ハロゲン原子により置換されていてもよいＣ₁〜₆アルキル基、ハロゲン原子により置換されていてもよいＣ₁〜₆アルキルオキシ基、シアノ基、またはニトロ基を示し、
Ｒ₁は、ハロゲン原子により置換されたＣ₁〜₆アルキル基を示す] 、
下記式で示されるアミン誘導体またはそれらの酸付加塩：

[Where
Ar is a halogen atom, a hydroxyl group or optionally substituted C ₁ to ₆ alkyl group by a halogen atom, optionally substituted C ₁ to ₆ alkyl group by a halogen atom, cyano group or a nitro group, pyridyl group which may be; or a halogen atom, optionally substituted C ₁ to ₄ alkyl group by a halogen atom, optionally substituted C ₁ to ₄ alkyl group by a halogen atom, a hydroxyl group, a cyano group Or a pyrimidyl group optionally substituted with a nitro group,
Y is a hydrogen atom, a halogen atom, a hydroxyl group, a substituted C ₁ optionally _1-6 alkyl group by a halogen atom, a substituted C ₁ optionally _1-6 alkyl group by a halogen atom, a cyano group or a nitro group, Indicate
R ₁ represents a C ₁ ~ ₆ alkyl group substituted by a halogen atom,
An amine derivative represented by the following formula or an acid addition salt thereof:

[式中、
Ａｒは、ハロゲン原子、水酸基、もしくはハロゲン原子により置換されていてもよいＣ₁〜₆アルキル基、ハロゲン原子により置換されていてもよいＣ₁〜₆アルキルオキシ基、シアノ基、またはニトロ基で置換されていてもよいピリジル基；あるいは、ハロゲン原子、ハロゲン原子により置換されていてもよいＣ₁〜₄アルキル基、ハロゲン原子により置換されていてもよいＣ₁〜₄アルキルオキシ基、水酸基、シアノ基、またはニトロ基で置換されていてもよいピリミジル基を示し、
Ｒ₁は、ハロゲン原子により置換されたＣ₁〜₆アルキル基を示す]
が挙げられる。

[Where
Ar is a halogen atom, a hydroxyl group or optionally substituted C ₁ to ₆ alkyl group by a halogen atom, optionally substituted C ₁ to ₆ alkyl group by a halogen atom, cyano group or a nitro group, pyridyl group which may be; or a halogen atom, optionally substituted C ₁ to ₄ alkyl group by a halogen atom, optionally substituted C ₁ to ₄ alkyl group by a halogen atom, a hydroxyl group, a cyano group Or a pyrimidyl group optionally substituted with a nitro group,
R ₁ represents a C ₁ ~ ₆ alkyl group substituted by a halogen atom]
Is mentioned.

  The pest control agent of the present invention can be used in combination or in combination with a microbial pesticide such as an entomopathogenic virus agent.

Examples of the bactericides used in combination or in combination include the following drugs (B-1) to (B-18).
(B-1) Examples of the nucleic acid synthesis inhibitor include benalaxyl, benalaxyl-M (benalaxyl-M), furaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), oxadixyl (oxadixyl) ), Offurace, bupirimate, dimethirimol, ethirimol, hymexazole, octhilinone, oxolinic acid and the like.
(B-2) Examples of mitotic and mitotic inhibitors include, for example, benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl , Dietofencarb, zoxamide, ethaboxam, pencycuron, fluopicolide and the like.
Examples of (B-3) complex I inhibitor include diflumetorim, tolfenpyrad, and the like.
(B-4) Complex II inhibitors include, for example, benodanil, flutolanil, mepronil, isofetamid, fluopyram, fenfuram, carboxin (carboxin) , Oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penflufen, penflufen (Penthiopyrad), sedaxane, boscalid and the like.
(B-5) Complex III inhibitors include, for example, azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin (Picoxystrobin), pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, cresoxim-methyl, trifloxystrobin, dimoxy Strobin (dimoxystrobin), phenaminostrobin (metaminostrobin), oryastrostrobin (orysastrobin), famoxadone, floxastrobin, mandestrobin, pyriminostrobin pyriminostrobin), fenamidone (fenamidone), pyribencarb (pyribencarb), cyazofamid (cyazofamid), amisulbrom (amisulbrom), Ametokutorajin (ametoctradin), and the like.
(B-6) Examples of the uncoupling inhibitor of oxidative phosphorylation include binapacryl, meptyldinocap, dinocap, fluazinam and the like.
Examples of (B-7) oxidative phosphorylation inhibitors include fentin acetate, fentin chloride, fentin hydroxide, and the like.
Examples of (B-8) ATP synthesis inhibitors include silthiofam.
(B-9) As amino acid and protein synthesis inhibitors, for example, cyprodinil, mepanipyrim, pyrimethanil, blasticidin-S, kasugamycin, streptomycin And oxytetracycline.
(B-10) Signaling inhibitors include, for example, quinoxyfen, proquinazid, fenpiclonil, fludioxonil, fludioxonate, chlozolinate, iprodione, procymidone, vinclozoline, (Vinclozolin).
(B-11) Examples of lipid and cell membrane synthesis inhibitors include edifenphos, iprobenfos, pyrazophos, isoprothione, biphenyl, chloroneb, and dichlorane. (Dicloran), quintozene, tecnazene, tolclofos-methyl, etridiazole, iodocarb, propamocarb, prothiocarb and the like.
(B-12) Examples of sterol synthesis inhibitors for membranes include, for example, triforine, pyrifenox, pyrizoxazole, fenarimol, nuarimol, imazalil, oxypoconazole (Oxpoconazole), pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, difenoconazole Diniconazole, epiconconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole iafol), hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, simeconazole, temeconazole (Tebuconazole), tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, aldimorph, dodemorph, fenpropimorph (Fenpropimorph), tridemorph (tridemorph), fenpropidin, piperalin, spiroxamine, fenhexamid, fenpyrazamine, fenib Kalb (pyributicarb), naftifine (naftifine), terbinafine (terbinafine), and the like.
(B-13) Cell wall biosynthesis inhibitors include, for example, validamycin, polyoxin, dimethomorph, flumorph, pyrimorph, benchthiavalicarb, iprovaricarb ( iprovalicarb), valifenalate, mandipropamid and the like.
(B-14) Cell wall melanin synthesis inhibitors include, for example, fthalide, pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil and the like.
(B-15) Host plant resistance inducers include, for example, acibenzolar-S-methyl, probenazole, thiadinyl, isothianil, laminarin and the like. Is mentioned.
(B-16) Examples of the multi-acting point contact activator include copper, sulfur, ferbam, mancozeb, maneb, metiram, propineb , Thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine guazatine), iminoctadine, anilazine, dithianon, quinoxaline (chinomethionat / quinomethionate), fluoroimide and the like.
(B-17) Other fungicides include, for example, cymoxanil, fosetyl-Al, phosphorous acid and salts, teclofthalam, triazoxide, flusulfamide , Diclomezine, metasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, flutolanil, ferimzone, tebufloquin, tebufloquin, tebufloquin Examples thereof include oxathiapiprolin, NNF-0721, MIF-1002, and NF-171.
(B-18) As plant disease control agents, JP2009-078991A, JP2009-073823A, WO2008 / 102678A, JP2010 / 083763A, and republication WO08 / 066614 shown below. No., re-publication WO 09/028280, WO 05/115994, JP 2006-290883, WO 07/072999, WO 07/108483, WO 08/062878, WO 06/098128 The compound of this is mentioned.

According to a preferred embodiment of the present invention, the compound represented by the formula (1) or a stereoisomer thereof is used as an agricultural and horticultural pest control agent (preferably an agricultural or horticultural insecticide and an agricultural and horticultural acaricide). be able to. According to a more preferred embodiment of the present invention, the compound represented by the formula (1) or a stereoisomer thereof is added to a plant parasitic mite pest control agent (preferably, mite (more preferably Tetranycus spider mite, Panonychus). It can be used as a spider mite or rust mite control agent). Plant parasitic mite pests can be effectively controlled even if they are drug resistant. Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used. The compound represented by the formula (1) is preferably R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ′ ₁ , R ′ _{2 in} the formula (1). , R ′ ₃ , and R ′ ₄ may be used in combination with the compound numbers 1 to 14 and 17 shown in Table 1.

According to a preferred embodiment of the present invention, the compound represented by the formula (1) or a stereoisomer thereof is used as an animal parasite control agent (preferably, an animal endoparasite control agent, an animal ectoparasite control agent, a sanitary pest control). And an unpleasant pest control agent). According to a more preferred aspect of the present invention, the compound represented by the formula (1) or a stereoisomer thereof can be used as an animal parasitic mite pest control agent (preferably, a tick family control agent). Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used. As the compound represented by the formula (1), a compound represented by the formula (1c) can be further used. The compound represented by the formula (1) is preferably R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ′ ₁ , R ′ _{2 in} the formula (1). , R ′ ₃ , and R ′ ₄ can be used in combination with the compound numbers 1 to 17 shown in Table 1.

  According to the present invention, there is provided a method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the compound represented by the formula (1) to the agricultural and horticultural pests or their growing place. According to the agricultural and horticultural pest control method of the present invention, an effective amount of the compound represented by the formula (1) is added to the agricultural and horticultural pest, plant, plant propagation material (for example, plant seed, plant foliage, Roots, germinated plants, seedlings, etc.), soil, nutrient solution in hydroponic culture, solid medium in hydroponic culture, or rooms that need to prevent infestation of pests. Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used.

  According to the present invention, there is provided a method for controlling animal parasites, which comprises applying an effective amount of the compound represented by formula (1) to the animal parasite or its place of growth. According to the method for controlling an animal parasite according to the present invention, an effective amount of the compound represented by the formula (1) is orally or injected into the body of the application animal, or the entire body surface of the application animal or There is provided a method of controlling comprising administering to a part. The animal parasite control method according to the present invention also comprises applying an effective amount of the compound represented by the formula (1) to a place where pest invasion, parasitism and migration are expected. A control method is provided. Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used. As the compound represented by the formula (1), a compound represented by the formula (1c) can be further used.

  According to this invention, use of the compound shown by Formula (1) in manufacture of the agricultural and horticultural pest control agent is provided. Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used.

  According to this invention, use of the compound shown by Formula (1) in manufacture of the parasite control agent for animals is provided. Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used. As the compound represented by the formula (1), a compound represented by the formula (1c) can be further used.

  According to the present invention, there is provided a compound represented by the formula (1) for use as an agricultural and horticultural pest control agent. Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used.

  According to the present invention, there is provided a compound represented by the formula (1) for use as an animal parasite control agent. Here, as the compound represented by the formula (1), a compound represented by the formula (1a) can be used. As the compound represented by the formula (1), a compound represented by the formula (1b) can also be used. As the compound represented by the formula (1), a compound represented by the formula (1c) can be further used.

  In another aspect, the present invention provides the following formula (1):

［式中、
Ｒ₁は、ノルマルプロピル基を示し、Ｒ₃およびＲ₅は、互いに異なって、水素原子またはノルマルプロピル基を示し、Ｒ₇はイソブチル基、ｓ−ブチル基、またはネオペンチル基を示し、
Ｒ₂、Ｒ₄、Ｒ₆、Ｒ₈は、同一または異なってよく、炭素数３〜７の直鎖のアルキル基を示し、
Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄は、同一または異なってよく、水素原子またはメチル基を示す（ただし、Ｒ₁およびＲ₃がノルマルプロピル基を示し、Ｒ₅が水素原子を示し、Ｒ₇がイソブチル基を示し、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈がいずれもノルマルペンチル基を示し、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄がいずれもメチル基を示す化合物、および、Ｒ₁およびＲ₅がノルマルプロピル基を示し、Ｒ₃が水素原子を示し、Ｒ₇がイソブチル基を示し、Ｒ₂、Ｒ₄、Ｒ₆およびＲ₈がいずれもノルマルペンチル基を示し、かつ、Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄がいずれもメチル基を示す化合物を除く。）。］で示される化合物またはその立体異性体を提供することができる。

[Where:
R ₁ represents a normal propyl group, R ₃ and R ₅ are different from each other and represent a hydrogen atom or a normal propyl group, R ₇ represents an isobutyl group, a s-butyl group, or a neopentyl group,
R ₂ , R ₄ , R ₆ and R ₈ may be the same or different and each represents a linear alkyl group having 3 to 7 carbon atoms;
R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ may be the same or different and each represents a hydrogen atom or a methyl group (provided that R ₁ and R ₃ represent a normal propyl group, and R ₅ represents a hydrogen atom). R ₇ represents an isobutyl group, R ₂ , R ₄ , R ₆ and R ₈ all represent a normal pentyl group, and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ Wherein R ₁ and R ₅ each represent a normal propyl group, R ₃ represents a hydrogen atom, R ₇ represents an isobutyl group, R ₂ , R ₄ , R ₆ and R ₈ Is a normal pentyl group, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are all methyl groups. Or a stereoisomer thereof can be provided.

  In this aspect, an agricultural and horticultural pest control agent comprising at least one of the above-mentioned compounds or stereoisomers thereof can be provided.

  In this aspect, it is possible to provide a method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the above-mentioned compound or stereoisomer thereof to agricultural or horticultural pests or their growing places.

  In the said aspect, use of the said compound or its stereoisomer for manufacturing the agricultural and horticultural pest control agent can be provided.

  In the said aspect, the said compound or its stereoisomer for using as an agricultural and horticultural pest control agent can be provided.

  In another aspect, the present invention provides the following formula (1):

［式中、
Ｒ₁は、ノルマルプロピル基を示し、Ｒ₃およびＲ₅は、互いに異なって、水素原子またはノルマルプロピル基を示し、Ｒ₇はイソブチル基、ｓ−ブチル基、またはネオペンチル基を示し、
Ｒ₂、Ｒ₄、Ｒ₆、Ｒ₈は、同一または異なってよく、炭素数３〜７の直鎖のアルキル基を示し、
Ｒ'₁、Ｒ'₂、Ｒ'₃、およびＲ'₄は、同一または異なってよく、水素原子またはメチル基を示す。］で示される化合物またはその立体異性体を提供することができる。

[Where:
R ₁ represents a normal propyl group, R ₃ and R ₅ are different from each other and represent a hydrogen atom or a normal propyl group, R ₇ represents an isobutyl group, a s-butyl group, or a neopentyl group,
R ₂ , R ₄ , R ₆ and R ₈ may be the same or different and each represents a linear alkyl group having 3 to 7 carbon atoms;
R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ may be the same or different and each represents a hydrogen atom or a methyl group. Or a stereoisomer thereof can be provided.

  In the said aspect, the parasite control agent for animals which comprises at least 1 or more types of the said compound or its stereoisomer can be provided.

In the said aspect, the control method of the animal parasite which comprises applying the effective amount of the said compound or its stereoisomer to the animal parasite or its growth place can be provided.
In this aspect, preferably, there is provided a method for controlling animal parasites, which comprises applying an effective amount of the compound or a stereoisomer thereof to the body surface of an animal parasitized by parasites. be able to.
In this aspect, preferably, a method for controlling an animal parasite is provided, which comprises orally administering an effective amount of the compound or a stereoisomer thereof to an animal parasitized by a parasite. it can.

  In the said aspect, use of the said compound or its stereoisomer for manufacturing the parasite control agent for animals can be provided.

  In the said aspect, the said compound or its stereoisomer for using it as a parasite control agent for animals can be provided.

  Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the examples.

The abbreviations described in the production examples are as follows. Fmoc is 9-fluorenylmethyloxycarbonyl, Me is methyl, Nva is norvaline, Nna is nonanyl, Ala is alanine, Gly is glycine, Leu is leucine, Hep is heptyl, OBn is benzyloxy, Bn is benzyl, OTag is It represents 3,4,5-tris (octadecyloxy) benzyloxy.
Production Example 1: Synthesis of (R)-(+)-2,3-epoxypropanoic acid benzyl ester 100 g of L-serine and 340 g of potassium bromide were dissolved in 600 ml of water at 0 ° C., and a 47% hydrogen bromide aqueous solution was added dropwise. When the reaction solution became homogeneous, 200 ml of 5N sodium nitrite solution was added dropwise, stirred at 0 ° C. for 30 minutes, and then stirred at room temperature for 24 hours. Diethyl ether was added to the reaction solution and extracted five times. The diethyl ether phase was dried over sodium sulfate and concentrated. The remaining residue was dissolved in ethanol, and a 9.5N potassium hydroxide ethanol solution was added dropwise at -40 ° C. After stirring at room temperature for 24 hours, the reaction solution was concentrated. The obtained white solid was suspended in ethanol and stirred at 60 ° C. for 1 hour, and then the white solid was collected by filtration with a Kiriyama funnel. The white solid collected by filtration was suspended in ethanol: water (39: 1) at 60 ° C. and stirred for 1 hour, and then the Kiriyama funnel white solid was collected by filtration. After performing this operation twice, it was dried well. 500 mg of the obtained white solid was dissolved in 8.3 ml of acetonitrile, 117 mg of 18-crown-6 ether and 0.57 ml of benzyl bromide were added, and the mixture was stirred at 40 ° C. for 13 hours. After returning the reaction solution to room temperature, diethyl ether was added, and the organic layer was washed with water and saturated brine, dried over sodium sulfate and concentrated. The obtained crude product was purified by flash column chromatography (n-hexane: ethyl acetate = 10: 1 to 9: 1) to obtain the desired (R)-(+)-2,3-epoxypropanoic acid benzyl ester. 529 mg was obtained.

[α] _D ²⁴ : + 18.3 ° (c = 0.82, CHCl ₃ )
1H-NMR (400 MHz, CDCl ₃ ): δ: 7.43-7.25 (m, 5H), 5.20 (dd, 2H), 3.46 (dd, 1H), 2.94 (dd, 2H) )
HR-MS (FAB, NBAmatrix): m / z [M + H] 178.1
Production Example 2: Synthesis of (R) -2-hydroxyheptanoic acid benzyl ester ((R) -Hep (OBn)) Suspended in ether, 107 ml of 0.91M n-butylmagnesium chloride in tetrahydrofuran was added dropwise, and the mixture was stirred at −78 ° C. for 30 minutes. 8.3 g of the compound of Production Example 1 was dissolved in 15 ml of anhydrous diethyl ether, added dropwise to the reaction solution at −78 ° C., and stirred at −78 ° C. for 30 minutes and at −5 ° C. for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction solution, the temperature was returned to room temperature, diethyl ether was added to separate the organic layer, and the organic layer was washed 3 times with a saturated aqueous ammonium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated, and the resulting crude product was purified by flash column chromatography (n-hexane: ethyl acetate = 20: 1 to 15: 1) to obtain the desired (R) -2. -11.1 g of hydroxy heptanoic acid benzyl ester was obtained.

Yield: quant.
[α] _D ²⁴ : + 18.0 ° (c = 0.93, CHCl ₃ )
1H-NMR (400 MHz, CDCl ₃ ): δ: 7.45-7.28 (m, 5H), 5.24 (d, J = 12.0 Hz, 1H), 5.19 (d, J = 12. 0 Hz, 1H), 4.23 (dd, J = 3.75, 7.20 Hz, 1H), 1.88-1.56 (m, 2H), 1.52-1.18 (m, 6H), 0.87 (t, J = 6.75Hz, 3H)
HR-MS (FAB, NBAmatrix): m / z [M + H] 236.1
Production Example 3: Synthesis of (R) -2-hydroxynonanoic acid benzyl ester (Bn- (R) -Nna ) 2 g of (R) -2-aminononanoic acid was dissolved in 160 ml of 2N sulfuric acid and stirred at room temperature with 2N 160 ml of an aqueous sodium nitrate solution was added dropwise and stirred at room temperature for 2 hours. Diethyl ether was added to the reaction solution and the mixture was extracted three times. The organic layer was dried over anhydrous sodium sulfate and concentrated.

  The obtained crude product was directly dissolved in 50 ml of methanol, and 5 ml of water was added. A 20% aqueous cesium carbonate solution was added until the pH of the solution reached 7.0, and then the solution was concentrated. It melt | dissolved in 5 ml of N, N- dimethylformamide, and 12.6 ml of benzyl bromide was dripped. After stirring at room temperature for 17 hours, water was added and extracted three times with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated, and the resulting crude product was purified by flash column chromatography (n-hexane: ethyl acetate = 30: 1) to obtain the desired (R) -2- 1.8 g of hydroxynonanoic acid benzyl ester was obtained.

Yield: 59%
1H-NMR (400 MHz, CDCl ₃ ): δ: 7.34-7.33 (m, 5H), 5.22 (dd, J = 12.2 Hz, 16.1 Hz, 2H), 4.25-4. 20 (m, 1H), 2.69 (d, 5.8 Hz, 1H), 1.82-1.75 (m, 1H), 1.67-1.60 (m, 1H), 1.42- 1.41 (m, 1H), 1.28-1.25 (m, 9H), 0.87 (t, J = 6.9 Hz, 3H)
MS (FAB, NBAmatrix): m / z [M + H] 264
Production Example 4: Synthesis of N-Fmoc-N-Me-L-Nva- (R) -Hep (OBn) In a nitrogen atmosphere, 2.3 g of the compound of Production Example 2 and 9-fluorenylmethyloxycarbonyl- at room temperature 4.2 g of N-methyl-L-norvaline was dissolved in 23 ml of dichloromethane, and 2.8 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and 60 mg of dimethylaminopyridine were added and stirred for 2 hours. Water was added to the reaction solution, and the mixture was extracted twice with chloroform. The obtained organic layer was washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by flash column chromatography (n-hexane: ethyl acetate = 15: 1 to 10: 1) to obtain the desired N-Fmoc-N-Me-L-Nva- (R) -Hep. (OBn) 5.4 g was obtained.
Production Example 5: Synthesis of N-Fmoc-N-Me-L-Nva- (R) -Hep (OTag) N-Fmoc-N-Me-L-Nva- (R) -Hep obtained in Production Example 4 1.3 g of (OBn) was dissolved in ethyl acetate, 249 mg of 10% palladium carbon was added, and the mixture was stirred at room temperature for 2 hours in a hydrogen atmosphere. The reaction solution was filtered through Celite, and the filtrate was concentrated to dryness. The obtained product was dissolved in dichloromethane, and 1.3 g of 3,4,5-tris (octadecyloxy) benzyl alcohol, 512 mg of N, N-dicyclohexylcarbodiimide and 8.9 mg of dimethylaminopyridine were added, and 1 hour 30 minutes. Stir. 100 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 200 ml of methanol cooled to 0 ° C., and then vacuum-dried to obtain 2.0 g of the target N-Fmoc-N-Me-L-Nva- (R) -Hep (OTag). It was.
Production Example 6: Synthesis of N-Fmoc-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep (OTag) N-Fmoc-N-Me-L- N-Fmoc- synthesized in the same manner as in Production Example 5 except that Nva- (R) -Hep (OBn) was changed to N-Fmoc-N-Me-L-Leu- (R) -Hep (OBn) 407 mg of N-Me-L-Leu- (R) -Hep (OTag) was dissolved in 5.6 ml of dichloromethane, 0.3 ml of piperidine was added, and the mixture was stirred at room temperature for 6 hours. 30 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 60 ml of methanol cooled to 0 ° C., and then vacuum-dried to obtain N-Me-L-Leu- (R) -Hep (OTag).

  On the other hand, N-Fmoc-N-Me-L-Gly- synthesized in the same manner as in Production Example 4 except that Fmoc-N-Me-L-Nva was changed to N-Fmoc-N-Me-L-Gly-. 804.1 mg of (R) -Hep (OBn) was dissolved in 30.4 ml of ethyl acetate, 160.8 mg of 10% palladium carbon was added, and the mixture was stirred at room temperature for 13 hours in a hydrogen atmosphere. The reaction solution was filtered through Celite, and the filtrate was concentrated to dryness to obtain N-Fmoc-N-Me-L-Gly- (R) -Hep.

The obtained crude N-Me-L-Leu- (R) -Hep (OTag) and crude N-Fmoc-N-Me-L-Gly- (R) -Hep were dissolved in 5.5 ml of dichloromethane, and diisopropylethylamine was dissolved. 0.15 ml and 0.2 g of PyBrop were added and stirred at room temperature for 22 hours. 30 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 60 ml of methanol cooled to 0 ° C., dried in vacuo, and the target N-Fmoc-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu -457 mg of-(R) -Hep (OTag) was obtained.
Production Example 7: N-Fmoc-N-Me-L-Nva- (R) -Hep-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep ( Synthesis of OTag) 1.1 g of the compound of Production Example 4 was dissolved in 37 ml of ethyl acetate, 212.0 mg of 10% palladium carbon was added, and the mixture was stirred at room temperature for 6 hours 30 minutes in a hydrogen atmosphere. The reaction solution was filtered through Celite, and the filtrate was concentrated to dryness to obtain N-Fmoc-N-Me-L-Nva- (R) -Hep.

  On the other hand, 457 mg of the compound of Production Example 6 was dissolved in 5.4 ml of dichloromethane, 0.3 ml of piperidine was added, and the mixture was stirred at room temperature for 4 hours. 30 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 60 ml of methanol cooled to 0 ° C., dried in vacuo, and N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep. (OTag) was obtained.

The resulting crude N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep (OTag) and crude N-Fmoc-N-Me-L-Nva- (R ) -Hep was dissolved in 5.7 ml of dichloromethane, 0.15 ml of diisopropylethylamine and 0.2 g of PyBrop were added, and the mixture was stirred at room temperature for 17 hours. 30 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 60 ml of methanol cooled to 0 ° C., dried in vacuo, and the target N-Fmoc-N-Me-L-Nva- (R) -Hep-N-Me-L-Gly -(R) -Hep-N-Me-L-Leu- (R) -Hep (OTag) 523.4 mg was obtained.
Production Example 8: N-Fmoc-N-Me-L-Nva- (R) -Hep-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep- Synthesis of N-Me-L-Nva- (R) -Nna (OTag) N-Fmoc-N- synthesized in the same manner as in Production Example 4 except that the compound of Production Example 2 was changed to the compound of Production Example 3. 310.6 mg of Me-L-Nva- (R) -Nna (OBn) was dissolved in 10.4 ml of ethyl acetate, 62.1 mg of 10% palladium carbon was added, and the mixture was stirred at room temperature for 1 hour 30 minutes in a hydrogen atmosphere. . The reaction solution was filtered through Celite, and the filtrate was concentrated to dryness to obtain N-Fmoc-N-Me-L-Nva- (R) -Nna.

  On the other hand, 122.0 mg of the compound of Production Example 7 was dissolved in 1.3 ml of dichloromethane, 0.1 ml of piperidine was added, and the mixture was stirred at room temperature for 4 hours. 10 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 20 ml of methanol cooled to 0 ° C., dried in vacuo, and N-Me-L-Nva- (R) -Hep-N-Me-L-Gly- (R) -Hep. -N-Me-L-Leu- (R) -Hep (OTag) was obtained.

The obtained crude N-Me-L-Nva- (R) -Hep-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep (OTag) and crude N-Fmoc-N-Me-L-Nva- (R) -Nna was dissolved in 1.3 ml of dichloromethane, 0.03 ml of diisopropylethylamine and 46.6 mg of PyBrop were added, and the mixture was stirred at room temperature for 13 hours. 10 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 20 ml of methanol cooled to 0 ° C., dried in vacuo, and the target N-Fmoc-N-Me-L-Nva- (R) -Hep-N-Me-L-Gly -(R) -Hep-N-Me-L-Leu- (R) -Hep-N-Me-L-Nva- (R) -Nna (OTag) 131.5 mg was obtained.
Production Example 9: Cycro (-N-Me-L-Nva- (R) -Hep-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep-N Synthesis of -Me-L-Nva- (R) -Nna-) (Compound 3) 131.5 mg of the compound of Preparation Example 8 was dissolved in 1.2 ml of dichloromethane, and 0.07 ml of piperidine was added thereto for 4 hours at room temperature. Stir. 10 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was collected by filtration, washed with 20 ml of methanol cooled to 0 ° C., and dried in vacuo. The resulting crude product was dissolved in 2.5 ml of 50% trifluoroacetic acid / dichloromethane and stirred at room temperature for 2 hours. 10 ml of methanol was added to the reaction solution and stirred at 0 ° C. for 1 hour. The resulting precipitate was filtered, washed with 20 ml of methanol cooled to 0 ° C., and the filtrate was concentrated to dryness. Crude N-Me-L-Nva- (R) -Hep-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep-N-Me- L-Nva- (R) -Nna was dissolved in 12.5 ml of dichloromethane, 0.05 ml of diisopropylethylamine and 65.2 mg of PyBOP were added, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution, 10% sodium hydrogen sulfate and saturated brine, dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by high performance liquid chromatography (eluent: acetonitrile: water = 90: 10 column: GL Sciences Inertsil ODS-SP 20 mm × 250 mm, flow rate 8.0 ml / min), and the target Cycro (− N-Me-L-Nva- (R) -Hep-N-Me-L-Gly- (R) -Hep-N-Me-L-Leu- (R) -Hep-N-Me-L-Nva- (R) -Nna-) (Compound 3) 25.8 mg was obtained.

  The compounds produced according to the method described in Production Example 9 and their physical properties are shown in Table 2 below.

製剤例１〔粒剤〕
化合物１ ５重量％
ベントナイト ４０重量％
タルク １０重量％
クレー ４３重量％
リグニンスルホン酸カルシウム ２重量％
製剤例２〔水和剤〕
化合物１ ３０重量％
クレー ５０重量％
ホワイトカーボン ２重量％
ケイソウ土 １３重量％
リグニンスルホン酸カルシウム ４重量％
ラウリル硫酸ナトリウム １重量％
上記成分を均一に混合し、粉砕して水和剤を得た。
製剤例３〔顆粒水和剤〕
化合物１ ３０重量％
クレー ６０重量％
デキストリン ５重量％
アルキルマレイン酸共重合物 ４重量％
ラウリル硫酸ナトリウム １重量％
上記成分を均一に粉砕混合し、水を加えてよく練合した後、造粒乾燥して顆粒水和剤を得た。
製剤例４〔フロアブル剤〕
化合物４ ２５重量％
ＰＯＥポリスチリルフェニルエーテル硫酸塩 ５重量％
プロピレングリコール ６重量％
ベントナイト １重量％
キサンタンガム１％水溶液 ３重量％
ＰＲＯＮＡＬ ＥＸ−３００（東邦化学工業株式会社） ０．０５重量％
ＡＤＤＡＣ ８２７（ケイ・アイ化成株式会社） ０．０２重量％
水 を加えて、１００重量％
上記配合からキサンタンガム１％水溶液と適当量の水を除いた全量を予備混合した後、湿式粉砕機にて粉砕した。その後、キサンタンガム１％水溶液と残りの水を加え、１００重量％としてフロアブル剤を得た。
製剤例５〔乳剤〕
化合物９ １５重量％
Ｎ，Ｎ−ジメチルホルムアミド ２０重量％
ソルベッソ１５０（エクソンモービル有限会社） ５５重量％
ポリオキシエチレンアルキルアリールエーテル １０重量％
上記成分を均一に混合、溶解して乳剤を得た。
製剤例６〔乳剤〕
化合物９ １重量％
ソルベッソ１５０（エクソンモービル有限会社） ５０重量％
ポリオキシエチレンアルキルアリールエーテル ５重量％
アルキルベンゼンスルホン酸カルシウム ５重量％
上記成分を均一に混合、溶解して乳剤を得た。
製剤例７〔粉剤〕
化合物４ ２重量％
クレー ６０重量％
タルク ３７重量％
ステアリン酸カルシウム １重量％
上記成分を均一に混合して粉剤を得た。
製剤例８〔ＤＬ粉剤〕
化合物４ ２重量％
ＤＬクレー ９４．５重量％
ホワイトカーボン ２重量％
ステアリン酸カルシウム １重量％
軽質流動パラフィン ０．５重量％
上記成分を均一に混合して粉剤を得た。
製剤例９〔微粒剤Ｆ〕
化合物１ ２重量％
キャリヤー ９４重量％
ホワイトカーボン ２重量％
ハイゾールＳＡＳ−２９６ ２重量％
上記成分を均一に混合して粉剤を得た。
製剤例１０〔液化滴剤〕
化合物２ １０重量％
ベンジルアルコール ７４．９重量％
プロピレンカーボネート １５重量％
ＢＨＴ ０．１重量％
上記成分を均一に攪拌、溶解して液化滴剤を得た。
製剤例１１〔液化滴剤〕
化合物３ ４８重量％
エタノール ５２重量％
上記成分を均一に混合して液化滴剤を得た。
試験例１：ナミハダニ黄緑型(Tetranychus uruticae) 成虫防除試験
ポット栽培のインゲンから直径２．８ｃｍのリーフディスクを切り抜き、これにナミハダニ成虫７頭を接種した。これに５０％アセトン水（Ｔｗｅｅｎ２０ ０．０５％加用）となるように調製した所定濃度の本発明化合物の薬液を茎葉処理し、風乾後、２５℃の恒温室内（１６時間明期−８時間暗期）に放置した。薬剤処理５日後に死亡虫数をカウントし、次式に従って殺虫率を算出した。２連制試験で行った。

Formulation Example 1 [Granule]
Compound 1 5% by weight
Bentonite 40% by weight
Talc 10% by weight
43% by weight of clay
2% by weight calcium lignin sulfonate
Formulation Example 2 [wettable powder]
Compound 1 30% by weight
50% by weight of clay
2% white carbon
Diatomaceous earth 13% by weight
Calcium lignin sulfonate 4% by weight
Sodium lauryl sulfate 1% by weight
The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.
Formulation Example 3 [Granule wettable powder]
Compound 1 30% by weight
60% clay
Dextrin 5% by weight
Alkyl maleic acid copolymer 4% by weight
Sodium lauryl sulfate 1% by weight
The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain a granular wettable powder.
Formulation Example 4 [Flowable Agent]
Compound 4 25% by weight
POE polystyryl phenyl ether sulfate 5% by weight
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
PRONAL EX-300 (Toho Chemical Co., Ltd.) 0.05% by weight
ADDAC 827 (Kay Kasei Co., Ltd.) 0.02% by weight
100% by weight with water
A total amount of xanthan gum 1% aqueous solution and an appropriate amount of water excluding the above mixture was premixed and then pulverized with a wet pulverizer. Thereafter, a 1% aqueous solution of xanthan gum and the remaining water were added to obtain a flowable agent at 100% by weight.
Formulation Example 5 [Emulsion]
Compound 9 15% by weight
N, N-dimethylformamide 20% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 55% by weight
10% by weight of polyoxyethylene alkyl aryl ether
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.
Formulation Example 6 [Emulsion]
Compound 9 1% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 50% by weight
Polyoxyethylene alkyl aryl ether 5% by weight
Calcium alkylbenzenesulfonate 5% by weight
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.
Formulation Example 7 [powder]
Compound 4 2% by weight
60% clay
Talc 37% by weight
Calcium stearate 1% by weight
The said component was mixed uniformly and the powder agent was obtained.
Formulation Example 8 [DL powder]
Compound 4 2% by weight
DL clay 94.5% by weight
2% white carbon
Calcium stearate 1% by weight
Light liquid paraffin 0.5% by weight
The said component was mixed uniformly and the powder agent was obtained.
Formulation Example 9 [Fine Granule F]
Compound 1 2% by weight
Carrier 94% by weight
2% white carbon
Hyzol SAS-296 2% by weight
The said component was mixed uniformly and the powder agent was obtained.
Formulation Example 10 (Liquid drops)
Compound 2 10% by weight
Benzyl alcohol 74.9% by weight
15% by weight propylene carbonate
BHT 0.1% by weight
The above components were uniformly stirred and dissolved to obtain a liquefied droplet.
Formulation Example 11 [Liquid drops]
Compound 3 48% by weight
Ethanol 52% by weight
The said component was mixed uniformly and the liquid drop was obtained.
Test Example 1: Nite spider mite (Tetranychus uruticae) Adult leaf tester 2.8 cm in diameter was cut out from a green bean grown on an adult control test pot, and 7 adult spider mite were inoculated. This was treated with a chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (addition of 0.05% Tween 20), air-dried, and then in a constant temperature room at 25 ° C (16 hours light period-8 hours) (Dark period). The number of dead insects was counted 5 days after the drug treatment, and the insecticidal rate was calculated according to the following formula. A two-run test was conducted.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead)] × 100
As a result, in 50 ppm foliage treatment, the compounds 1, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14 and 17 of the present invention have a high insecticidal activity with a death rate of 80% or more. Indicated.
Test example 2: Nite spider mite (Tetranychus uruticae) Egg control test A leaf disc having a diameter of 2.0 cm was cut out from a green bean grown in a pot, and 5 adult females of a spider mite were inoculated into this and laid in a thermostatic chamber at 25 ° C. . After 24 hours, the female adults were removed from the leaf disc, and the chemical solution of the compound of the present invention prepared at a predetermined concentration so as to be 50% acetone water (added 0.05% Tween 20) was treated with foliage. After air drying, it was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). Seven days after the drug treatment, the number of remaining eggs and the number of dead insects were counted, and the egg-killing / insecticidal rate was calculated according to the following formula. A two-run test was conducted.

Egg kill / insecticidal rate (%) = {(number of remaining eggs + number of dead insects) / (number of remaining eggs + number of dead insects + number of surviving insects)} × 100
As a result, in 50 ppm immersion treatment, the compounds 1, 3, 4, 5, 7, 8, 9, 11, 12, 13 and 14 of the present invention showed high insecticidal activity with an ovicidal / insecticidal rate of 80% or more. .
Test Example 3: Tetranychus kanzawai adult control test A leaf disc having a diameter of 2.8 cm was cut out from a bean grown in a pot and inoculated with 7 Kanzawa spider mites . A chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (addition of 0.05% Tween 20) was treated with stems and leaves, air-dried, and then kept in a constant temperature room at 25 ° C (16 hours light period-8 hours) (Dark period). Two days after drug treatment, the number of dead insects was counted, and the insecticidal rate was calculated according to the following formula. A two-run test was conducted.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead)] × 100
As a result, the compound 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 and 14 of the present invention have a high mortality rate (%) of 80% or more by 50 ppm foliage treatment. Insecticidal activity was demonstrated.
Test Example 4: Kanzawa spider mite (Tetranychus kanzawai) egg control test A leaf disc having a diameter of 2.0 cm was cut out from a bean grown in a pot and inoculated with 7 female females of the spider mite of Kanzawa and spawned in a thermostatic chamber at 25 ° C. After 24 hours, adult female worms were removed from the leaf disc, and a foliage treatment was carried out with a chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (added 0.05% Tween 20). After air drying, it was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). Six days after the drug treatment, the number of remaining eggs and the number of dead insects were counted, and the egg-killing / insecticidal rate was calculated according to the following formula. A two-run test was conducted.

Egg kill / insecticidal rate (%) = {(number of remaining eggs + number of dead insects) / (number of remaining eggs + number of dead insects + number of surviving insects)} × 100
As a result, the compounds 1, 7 and 9 of the present invention exhibited a high insecticidal activity with an egg killing / insecticidal rate (%) of 80% or more after 50 ppm of foliage treatment.
Test example 5: Panonychus citri egg control test A leaf disc having a diameter of 2.0 cm was cut out from a pot-grown Iyokan, and 7 female adults of the citrus spider mite were inoculated therein and allowed to lay eggs in a thermostatic chamber at 25 ° C. After 24 hours, adult female worms were removed from the leaf disc, and a foliage treatment was carried out with a chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (added 0.05% Tween 20). After air drying, it was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). After 9 days of drug treatment, the number of remaining eggs and the number of dead insects were counted, and the egg-killing / insecticidal rate was calculated according to the following formula. A two-run test was conducted.

Egg kill / insecticidal rate (%) = {(number of remaining eggs + number of dead insects) / (number of remaining eggs + number of dead insects + number of surviving insects)} × 100
As a result, the compounds 1, 3, 4, 5, 6, 8, 9, 10, 12 and 13 of the present invention showed a high insecticidal activity with an egg-killing / insecticidal rate (%) of 80% or more after 50 ppm foliage treatment. It was.
Test Example 6: Drug-resistant Nite spider mite (Tetranychus urticae) A leaf disc having a diameter of 2.8 cm was cut out from a green bean grown on an adult control test pot, and 7 drug-resistant Nite mite mite were inoculated into this. This was treated with a chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (addition of 0.05% Tween 20), air-dried, and then in a constant temperature room at 25 ° C (16 hours light period-8 hours) (Dark period). The number of dead insects was counted 5 days after the drug treatment, and the insecticidal rate was calculated according to the following formula. A two-run test was conducted.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead)] × 100
As a result, the compounds 1, 3, 4, 5, 6, 9, and 14 of the present invention showed high insecticidal activity with a mortality rate of 80% or more in the treatment of 5 ppm of foliage.

In addition, as a result of testing the control drug acequinosyl by 10 ppm foliar treatment, the insecticidal rate against the yellow spider mite of the sensitive strain was 100%. On the other hand, the insecticidal rate by the 10 ppm foliar treatment of acequinosyl against the drug resistant strain Nami-tani yellow-green type adult used in this test was 90%. That is, it was found that the compound according to the present invention can effectively control even drug-resistant pests.
Test Example 7: Drug-resistant Nite spider mite (Tetranychus urticae) Egg control test A leaf disc having a diameter of 2.0 cm was cut out from a green bean grown in a pot, and this was inoculated with 5 female spider mite adults in a thermostatic chamber at 25 ° C. Spawned. After 24 hours, the female adults were removed from the leaf disc, and the chemical solution of the compound of the present invention prepared at a predetermined concentration so as to be 50% acetone water (added 0.05% Tween 20) was treated with foliage. After air drying, it was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). Seven days after the drug treatment, the number of remaining eggs and the number of dead insects were counted, and the egg-killing / insecticidal rate was calculated according to the following formula. A two-run test was conducted.

Egg kill / insecticidal rate (%) = {(number of remaining eggs + number of dead insects) / (number of remaining eggs + number of dead insects + number of surviving insects)} × 100
As a result, the compounds 1, 3, 4, 9 and 14 of the present invention showed a high insecticidal activity with an ovicidal / insecticidal rate of 80% or more at 5 ppm of foliage treatment.

In addition, as a result of testing the control drug acequinosyl by 10 ppm foliar treatment, the ovicidal / insecticidal rate for the yellow spider mite of the sensitive strain was 100%. On the other hand, the ovicidal / insecticidal rate by treatment with 10 ppm foliage of acequinosyl for the drug-resistant strain Nami-tani yellow-green type egg used in this test was 11%. That is, it was found that the compound according to the present invention can effectively control even drug-resistant pests.

Test example 8: Plutella xylostella control test A leaf disc having a diameter of 5.0 cm was cut out from a cabbage grown in a pot, and a 50% acetone water (addition of 0.05% Tween 20) was added to the leaf disk. A chemical solution of the compound of the present invention was sprayed. After air drying, the 2nd instar larvae were released. Thereafter, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. A two-run test was conducted.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead)] × 100
As a result, the compound 12 of the present invention showed a high insecticidal activity with a mortality rate of 80% or more by spraying with 200 ppm.
Test Example 9: Cotton aphid (Aphis gossypii) control test A leaf disk having a diameter of 2.0 cm was cut out from a cucumber grown in a pot, and a predetermined concentration prepared so as to be 50% acetone water (added 0.05% Tween 20) to this. The chemical solution of the present compound was sprayed. After air drying, the first instar larvae were released. Thereafter, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. A two-run test was conducted.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead insects)] x 100
As a result, the compounds 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 12, 13 and 14 of the present invention showed an insecticidal activity of 80% or more by treatment with 100 ppm of foliage.
Moreover, the compound 1 of this invention showed the high insecticidal activity with a mortality rate of 80% or more by the dispersion | spreading process of 1.25 ppm.
Test example 10: Frankliniella occidentalis control test A leaf disk having a diameter of 2.8 cm was cut out from a green bean grown in a pot, and a 50% acetone water (addition of 0.05% Tween 20) was prepared for this. A chemical solution of the present compound at a concentration was sprayed. After air drying, the first instar larvae were released. Thereafter, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for viability 6 days after release, and the mortality was calculated according to the following formula. A two-run test was conducted.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead)] × 100
As a result, the compounds 1, 2, 3, 4 and 5 of the present invention showed an insecticidal activity of 80% or more by treatment with 200 ppm of foliage.
Test example 11: Onale whitefly (Trialeurodes vaporariorum) control test Onsite whitefly adults were released in a pot-cultivated cucumber and allowed to lay eggs for 2 days. After the egg-laying was completed, a leaf disc having a diameter of 2.0 cm was cut out from the cucumber and the egg-laying was confirmed. . After spraying, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The mortality of the insects was observed 12 days after spraying, and the death rate was calculated according to the following formula. A two-run test was conducted.

Mortality rate (%) = [(number of eggs laid−number of surviving insects) / number of eggs laid] × 100
As a result, the compounds 1, 2, 3, 4, 5, 6, 9, and 11 of the present invention showed high insecticidal activity with a mortality rate of 80% or more by spraying with 100 ppm.
Test Example 12: Trigonotylus caelestialium control test 50% acetone water (added with 0.05% Tween 20) to a chemical solution of the compound of the present invention prepared at a predetermined concentration 4 days after sowing The part was immersed for 30 seconds. After air-drying, this was put in a glass tube, and further, 2 second-instar larvae of red bearded winged mosquito were released in the same glass tube. After releasing, the tube was covered and left in a constant temperature room at 25 ° C. In order to supply water to the wheat during the test, the wheat was sucked from below the glass tube. Four days after the treatment, the larvae were observed for survival, and the mortality was calculated according to the following formula. A three-run test was conducted.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead)] × 100
As a result, the compounds 3, 5, 8 and 11 of the present invention exhibited a high insecticidal activity with a death rate of 80% or more after 50 ppm immersion treatment.
Test Example 13: Haemaphysalis longicornis Control Test A capsule having a diameter of 2 cm and a height of 2 cm was adhered to the back of the mouse. 9.5 μg of the compound of the present invention and Verticilide were dissolved in ethanol and dropped onto the surface of the mouse body in the capsule. After sufficiently drying, 10 young tick mites were released, and the upper part of the capsule was sealed with a lid. Mice were kept in cages at 25 ° C., 12 hours light period, 12 hours dark period. Five days after release, the capsules were removed, the number of young mites lived and dead, and the number of blood-sucking individuals was counted.

Death bitter worm rate (%) = [number of dead bitter worms / (number of living insects tens of dead bitter worms)] × 100
As a result, at a treatment amount of 9.5 μg, the compounds 1, 3 and 5 of the present invention showed a high insecticidal activity with a death reptile rate of 65% or more, and the compounds 15 and 16 of the present invention with a death reptile rate of 90% or more. It was. However, Verticilide showed no insecticidal activity.
Test Example 14: Catenoid (Ctenocephalides felis) Control Test A petri dish having a diameter of 5 cm and a height of 2 cm was adhered to the back surface of a dog. 2.14 mg of the compound of the present invention was dissolved in ethanol and added dropwise to the dog body surface in a petri dish. After sufficiently drying, 30 adult cat fleas were released and the top of the petri dish was sealed with a lid. Dogs were raised in cages under conditions of 25 ° C., 12 hours light period, 12 hours dark period. Three days after release, the petri dish was removed and the number of live and dead fleas and blood-sucking individuals was measured, and the death rate was calculated according to the following formula.

Death rate (%) = [Number of dead insects / (Number of living insects tens of dead agony insects)] × 100
As a result, the compound 15 of the present invention showed a high insecticidal activity with a mortality rate of 100% at a treatment amount of 2.14 mg.
Test Example 15: Haemaphysalis longicornis control test An ethanol solution of the compound of the present invention was orally administered to dogs at a dose of 40 mg / kg body weight as the present compound. Five days after administration of the drug, about 50 spider mites per insect were released. Seven days after drug administration, the number of surviving spider mites on dogs was counted and compared with the negative control group to which only ethanol was administered, and the extinction rate of spider spider mites was calculated according to the following formula.

Rate of extermination (%) = [(average number of survival in negative control group−number of survival in group administered with compound of the present invention) / number of survival in negative control group] × 100
As a result, the compound 15 of the present invention showed a control rate of 100%.

Claims (14)

Following formula (1):

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. R ₆ and R ₈ are different from each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are identical to one another, R _'3 and R' ₄ are each, may be the same or different from the R _'1 and R'₂;
R ₁ , R ₃ , R ₅ , and R ₇ each represent a hydrogen atom, a normal propyl group, an isobutyl group, an s-butyl group, or a neopentyl group (provided that R ₁ and R ₃ are the same as each other) R ₅ is different from R ₁ and R ₃ , R ₇ is different from R ₁ , R ₃ , R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are 7 wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as or different from R ₂ and R ₄ , respectively. And R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom or a methyl group (provided that R ′ ₁ and R ′ ₂ are the same as each other, and R ′ ₃ and R _'4 are each, R' ₁ and R 'may be the ₂ different be the same but, R' different from each other and ₃ and R _'4 ); Or R ₁ and R ₃ represents an n-propyl group, R ₅ represents a hydrogen atom, R ₇ represents a s- butyl group or a neopentyl _{group, R 2, R 4, R} 6 and R ₈ are n-pentyl And a compound in which R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ represent a methyl group. Or a stereoisomer thereof. Following formula (1):

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. An optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are different from each other, R ₆ may be the same as or different from R ₂ , R ₄ and R ₈ ; R ₈ may be the same as or different from R ₂ , R ₄ and R ₆ ), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom, a methyl group, or an ethyl group (provided that R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other) Or R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms. Or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is , R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain having 1 to 9 carbon atoms, branched or A cyclic alkyl group or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms is shown (however, _2, R _4, R _6, and R ₈ may being the same or different), _{and, R '1, R' 2} , R '3, and R' ₄ are each a hydrogen atom, Represents a methyl group or an ethyl group (provided that R ′ ₁ and R ′ ₂ are different from each other; R ′ ₃ may be the same as or different from R ′ ₁ , R ′ ₂ and R ′ ₄ ; R ′ ₄ may be the same or different from R ′ ₁ , R ′ ₂ and R ′ ₃ ). Or a stereoisomer thereof. Following formula (1):

[Where:
R ₁ represents a normal propyl group, R ₃ and R ₅ are different from each other and represent a hydrogen atom or a normal propyl group, R ₇ represents an isobutyl group, a s-butyl group, or a neopentyl group,
R ₂ , R ₄ , R ₆ and R ₈ may be the same or different and each represents a linear alkyl group having 3 to 7 carbon atoms;
R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ may be the same or different and each represents a hydrogen atom or a methyl group (provided that R ₁ and R ₃ represent a normal propyl group, and R ₅ represents a hydrogen atom). R ₇ represents an isobutyl group, R ₂ , R ₄ , R ₆ and R ₈ all represent a normal pentyl group, and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ Wherein R ₁ and R ₅ each represent a normal propyl group, R ₃ represents a hydrogen atom, R ₇ represents an isobutyl group, R ₂ , R ₄ , R ₆ and R ₈ Is a normal pentyl group, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are all methyl groups. Or a stereoisomer thereof.   An agricultural and horticultural pest control agent comprising at least one of the compounds according to claims 1 to 3 or a stereoisomer thereof.   A method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the compound according to claim 1 or a stereoisomer thereof to agricultural or horticultural pests or a place where they grow.   Use of the compound according to claims 1 to 3 or a stereoisomer thereof for producing an agricultural and horticultural pest control agent.   The compound according to claim 1 or a stereoisomer thereof for use as an agricultural and horticultural pest control agent. The following formula (1a):

[Where
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. Or an alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are the same as each other, and R ₆ and R ₈ may be the same as R ₂ and R ₄ , respectively). it may be different), _{and, R '1, R' 2} , R '3, and R' ₄ are each, water Atom, a methyl group or an ethyl group, (wherein, R _'1 and R' ₂ are identical to one another, R _'3 and R' ₄ are each a same and R _'1 and R' ₂ Or different);
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, and are a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group having 1 to 9 carbon atoms, or Represents an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other, a hydrogen atom, a methyl group, or represents an ethyl group; or _{R 1, R 3, R 5} , and R ₇ are each a hydrogen atom, is substituted Linear which may having 1 to 9 carbon atoms have, branched, or indicates the cyclic alkyl group or an optionally substituted 2 to 9 carbon atoms alkoxyalkyl group, (wherein, R ₁ is, R _3, R ₅ and R ₇ , R ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom or an optionally substituted carbon number 1 to 9 linear, branched, or cyclic alkyl group, or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (provided that R ₄ is R ₂ , R _6, and R ₈ ; Unlike, R _2, R ₆ and R ₈ may be identical to each other, or, R ₈ is different from R _2, R ₄ and R _6, R _2, R ₄ and R ₆ are identical to each other ), _{and, R '1, R' 2} , R '3, and R' ₄ are identical to one another, a hydrogen atom, a methyl group Or an ethyl group. ] A compound represented by
The following formula (1b):

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain, branched or cyclic alkyl group having 1 to 9 carbon atoms, or a substituted group. An optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₂ and R ₄ are different from each other, R ₆ may be the same as or different from R ₂ , R ₄ and R ₈ ; R ₈ may be the same as or different from R ₂ , R ₄ and R ₆ ), and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ each represent a hydrogen atom, a methyl group, or an ethyl group (provided that R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other) Or R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms. Or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (wherein R ₁ and R ₃ are the same as each other, R ₅ is different from R ₁ and R _3, and R ₇ is , R ₁ , R ₃ , and R ₅ ), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom, an optionally substituted straight chain having 1 to 9 carbon atoms, branched or A cyclic alkyl group or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms is shown (however, _2, R _4, R _6, and R ₈ may being the same or different), _{and, R '1, R' 2} , R '3, and R' ₄ are each a hydrogen atom, Represents a methyl group or an ethyl group (provided that R ′ ₁ and R ′ ₂ are different from each other; R ′ ₃ may be the same as or different from R ′ ₁ , R ′ ₂ and R ′ ₄ ; R ′ ₄ may be the same or different from R ′ ₁ , R ′ ₂ and R ′ ₃ ). Or a compound represented by the following formula (1c):

[Where:
R ₁ , R ₃ , R ₅ , and R ₇ are each a hydrogen atom, an optionally substituted linear, branched, or cyclic alkyl group having 1 to 9 carbon atoms, or an optionally substituted carbon. Represents an alkoxyalkyl group of 2 to 9, wherein R ₁ and R ₅ are the same as each other, R ₃ is different from R ₁ and R _5, and R ₇ is R ₁ , R ₃ , R ₅ R ₂ , R ₄ , R ₆ and R ₈ are the same as each other, and are a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group having 1 to 9 carbon atoms, or Represents an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms, and R ′ ₁ , R ′ ₂ , R ′ ₃ , and R ′ ₄ are the same as each other, a hydrogen atom, a methyl group, or represents an ethyl group; or _{R 1, R 3, R 5} , and R ₇ are each a hydrogen atom, is substituted Linear which may having 1 to 9 carbon atoms have, branched, or indicates the cyclic alkyl group or an optionally substituted 2 to 9 carbon atoms alkoxyalkyl group, (wherein, R ₁ is, R _3, R ₅ and R ₇ , R ₃ , R ₅ and R ₇ are the same as each other), R ₂ , R ₄ , R ₆ and R ₈ are each a hydrogen atom or an optionally substituted carbon number 1 to 9 linear, branched, or cyclic alkyl group, or an optionally substituted alkoxyalkyl group having 2 to 9 carbon atoms (provided that R ₆ is R ₂ , R _4, and R ₈ ; R ₂ , R ₄ and R ₈ are the same as each other), and R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ are the same as each other, and are a hydrogen atom, a methyl group, or An ethyl group is shown. ] The parasite control agent for animals which comprises at least 1 or more types of the compound shown by these, or those stereoisomers. Following formula (1):

[Where:
R ₁ represents a normal propyl group, R ₃ and R ₅ are different from each other and represent a hydrogen atom or a normal propyl group, R ₇ represents an isobutyl group, a s-butyl group, or a neopentyl group,
R ₂ , R ₄ , R ₆ and R ₈ may be the same or different and each represents a linear alkyl group having 3 to 7 carbon atoms;
R ′ ₁ , R ′ ₂ , R ′ ₃ and R ′ ₄ may be the same or different and each represents a hydrogen atom or a methyl group. Or a stereoisomer thereof.   A method for controlling animal parasites, which comprises applying an effective amount of the compound according to claim 8 or 9 or a stereoisomer thereof to the animal parasite or its place of growth. The animal parasite according to claim 10, which comprises applying an effective amount of the compound according to claim 8 or 9 or a stereoisomer thereof to the body surface of an animal parasitized by the parasite. Control method. Control of animal parasites according to claim 10, comprising orally administering an effective amount of a compound according to claim 8 or 9 or a stereoisomer thereof to an animal parasitized by parasites. Method.   Use of the compound according to claim 8 or 9 or a stereoisomer thereof for producing an animal parasite control agent.   The compound according to claim 8 or 9, or a stereoisomer thereof, for use as an animal parasite control agent.